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β-D-呋喃核糖基异硫氰酸三苯甲酸酯 | 58214-53-2

分子结构分类

有机化合物 - 有机氧化合物

中文名称

β-D-呋喃核糖基异硫氰酸三苯甲酸酯

中文别名

2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖基异硫氰酸酯

英文名称

2,3,5-tri-O-benzoyl-β-D-ribofuranosyl isothiocyanate

英文别名

2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl-isothiocyanat；2,3,5-tri-O-benzoyl-β-D-ribofuranosylisothiocyanate；tri-O-benzoyl-β-D-ribofuranosyl isothiocyanate；2,3,5-Tri-O-benzoyl-β-D-ribofuranosylisothiocyanat；2.3.5-Tri-O-benzoyl-β-D-ribofuranosylisothiocyanat；[(2R,3R,4R,5R)-3,4-Dibenzoyloxy-5-isothiocyanatooxolan-2-yl]methyl benzoate

CAS

58214-53-2

化学式

C₂₇H₂₁NO₇S

mdl

——

分子量

503.532

InChiKey

AWVSFHIUQVIIOW-MOUTVQLLSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

6.2
重原子数：

36
可旋转键数：

11
环数：

4.0
sp3杂化的碳原子比例：

0.19
拓扑面积：

133
氢给体数：

0
氢受体数：

9

安全信息

WGK Germany：

3

SDS

SDS：76e6b3d78f8462c3b2af68adf5c6488c

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: 2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl
Product name
isothiocyanate
CAS-No. : 58214-53-2
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No 1272/2008
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: β-D-ribofuranosyl isothiocyanate tribenzoate
Synonyms
Formula : C27H21NO7S
Molecular Weight : 503,52 g/mol

Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Sulphur oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
hygroscopic Store under inert gas.
Specific end uses
no data available

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

SECTION 15 - REGULATORY INFORMATION
N/A

SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖	1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose	6974-32-9	C₂₈H₂₄O₉	504.493
——	2,3,5-tri-O-benzoyl-α-D-ribofuranosyl chloride	50909-47-2	C₂₆H₂₁ClO₇	480.902
——	2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride	5991-01-5	C₂₆H₂₁ClO₇	480.902
——	2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide	16205-60-0	C₂₆H₂₁BrO₇	525.353
——	2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide	22860-91-9	C₂₆H₂₁BrO₇	525.353

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	N-[4-(methoxycarbonyl)benzyl]-N'-(2,3,5-tribenzoyl-β-D-ribofuranosyl)carbodiimide	——	C₃₆H₃₀N₂O₉	634.642
——	tri-O-benzoyl-N-[1,2,3,4]thiatriazol-5-yl-β-D-ribofuranosylamine	65934-38-5	C₂₇H₂₂N₄O₇S	546.56
——	(5R)-5-hydroxy-5-(D-arabino-tetritol-1-yl)-1-(2',3',4'-tri-O-benzoyl-β-D-ribofuranosyl)imidazolidine-2-thione	——	C₃₃H₃₄N₂O₁₂S	682.705
——	(5R)-5-hydroxy-3-methyl-5-(D-arabino-tetritol-1-yl)-1-(2',3',4'-tri-O-benzoyl-β-D-ribofuranosyl)imidazolidine-2-thione	——	C₃₄H₃₆N₂O₁₂S	696.732
——	(S)-1-[4-(methoxycarbonyl)benzyl]-2-(2',3',5'-tribenzoyl-β-D-ribofuranosyl)amino-4-phenyl-4,5-dihydro-6-pyrimidinone	385433-37-4	C₄₅H₃₉N₃O₁₀	781.819

反应信息

作为反应物：

描述：

β-D-呋喃核糖基异硫氰酸三苯甲酸酯在 sodium methylate 、三乙胺、三苯基膦作用下，以甲醇、二氯甲烷、甲苯为溶剂，反应 14.0h，生成

参考文献：

名称：

Synthesis of Novel Guanidinoglycoside: 2-Glycosylamino 4,5-dihydro-6-pyrimidinone

摘要：

DOI：

10.1021/jo015915q
作为产物：

描述：

1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖在盐酸、乙酰氯作用下，以丙酮为溶剂，反应 2.0h，生成 β-D-呋喃核糖基异硫氰酸三苯甲酸酯

参考文献：

名称：

糖呋喃糖基异硫氰酸酯的简便合成

摘要：

摘要在正常条件下，由无水丙酮中的硫氰酸钾与相应的糖基氯反应，可在相应的糖基氯条件下，在光滑的条件下，于平滑的条件下获得过酰基化的呋喃呋喃糖基异硫氰酸酯，这是糖基吡喃糖基硫氰酸酯合成的经典条件。在呋喃糖酶的情况下，没有获得糖基硫氰酸酯，并且该方法立体选择性地产生1，2-反式异硫氰酸酯，产率超过80％。

DOI：

10.1016/s0008-6215(97)00242-5

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文献信息

A Novel, Simple Cyclocondensation Reaction Towards Glycosyl Triazines

作者：David Deniaud、Vincent Kikelj、Karine Julienne、Pascal Janvier、Jean-Claude Meslin

DOI：10.1055/s-0028-1083156

日期：——

Sugars bearing an isothiocyanate moiety at C-1 react with diazadienium iodide to afford glycosyl triazines that represent, through an easy cyclocondensation reaction step, a flexible entry to different nucleoside analogues. We herein demonstrate that this [4+2] cycloaddition reaction occurs with total regiocontrol and good yields. Subsequent transformation of the thiocarbonyl into a carbonyl, and nucleophilic substitution of the methylsulfanyl group by ammonia, yields the 5-azacytidine analogues. All compounds were fully characterised by IR, HRMS, and ¹³C and ¹H NMR (COSY, HMBC and HMQC).

在C-1位带有异硫氰酸基团的糖与二氮二烯丙碘反应生成糖基三嗪类化合物，这些化合物通过一步简单的环加成反应，提供了一种灵活的途径来制备不同的核苷类似物。我们在此证明，这种[4+2]环加成反应具有完全的区域选择性和良好的产率。随后将硫羰基转化为羰基，并通过氨对甲硫基进行亲核取代，得到了5-氮胞苷类似物。所有化合物均通过IR、HRMS以及¹³C和¹H NMR（包括COSY、HMBC和HMQC）进行了全面的表征。
An Efficient Route to Pyrimidine Nucleoside Analogues by [4 + 2] Cycloaddition Reaction

作者：Morwenna S. M. Pearson、Aélig Robin、Nathalie Bourgougnon、Jean Claude Meslin、David Deniaud

DOI：10.1021/jo034709a

日期：2003.10.1

synthesis for pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction. These compounds were obtained by convergent chemistry from glycosyl isothiocyanates 3a-f (pyranoses, furanoses, and dissaccharides) and diazadienium salt 5. In fact, diazapentadienium iodide 5 prepared from vinylthioamide 4 is an efficient intermediate in heterocyclic synthesis and reacts with isothiocyanates 3a-f affording

我们在这里报告通过[4 + 2]环加成反应合成嘧啶核苷类似物的有效方法。这些化合物是通过收敛化学从糖基异硫氰酸酯3a-f（吡喃糖，呋喃糖和二糖）和二氮杂鎓盐5中获得的。实际上，由乙烯基硫酰胺4制备的碘化二戊戊二烯碘化物5是杂环合成中的有效中间体，并与异硫氰酸酯3a-f反应以高收率和完全的区域控制提供β-D-尿嘧啶类似物7a-f。所有化合物均通过IR，HRMS，13C和1H NMR（COSY和HMQC）充分表征。
Studies on nucleoside analogs. XX. Syntheses of 1,2,4-triazole and 1,3,5-triazine glycosides.

作者：HARUO OGURA、HIROSHI TAKAHASHI、OSAMU SATO

DOI：10.1248/cpb.29.1838

日期：——

The reaction of glycosyl isothiocyanate (1a) with thiourea in the presence of Mel-NEt3 gave a di-SMe compound (2a) and a mono-SMe compound (3a). Glycosyl isothiocyanates (1a, b, and c) reacted with amidino compounds (HN=CRNH3 ; R=H, Me, OMe, SMe, NH2) to afforded the corresponding glycosyl isothiobiurets (3a, c, and 6a, b), N-glycosyl-N'-amidino thioureides (4a, b, and 5a, b) or N-glycosyl-N'-guanidyl thioureides (7a and b) in good yields. Treatment of 3a, 6b, or 7a, b with HC (OEt)3 gave the corresponding s-triazine glycosides (8a, 9a, b, and 10b) in fair yields. On the other hand, similar treatment of 4a, b or 5a, b with HC (OEt)3 did not give s-triazine glycosides, but the starting material was recovered. N-Bromosuccinimide oxidation of 4a, b, 5a, b, 3a, c or 7a, b gave the corresponding 5-substituted-1, 2, 4-triazole-3-thiones (11a, b, 12a, b, or 14a, b) in excellent yields.

在 Mel-NEt3 存在下，异硫氰酸糖基酯（1a）与硫脲反应生成二-SMe 化合物（2a）和单-SMe 化合物（3a）。糖基异硫氰酸酯（1a、b 和 c）与脒基化合物（HN=CRNH3；R=H、Me、OMe、SMe、NH2）反应，得到相应的糖基异硫脲（3a、c 和 6a、b）、N-糖基-N'-脒基硫脲（4a、b 和 5a、b）或 N-糖基-N'-胍基硫脲（7a 和 b），产率良好。用 HC (OEt)3 处理 3a、6b 或 7a、b 可以得到相应的 s-三嗪苷（8a、9a、b 和 10b），收率尚可。另一方面，用 HC (OEt)3 对 4a, b 或 5a, b 进行类似处理并不能得到 s-三嗪苷，但可以回收起始物质。4a、b、5a、b、3a、c 或 7a、b 的 N-溴代丁二酰亚胺氧化反应得到了相应的 5-取代-1，2，4-三唑-3-硫酮（11a、b、12a、b 或 14a、b），收率极高。
Studies on nucleoside analogs. XXII. Reactions of glycosyl isothiocyanates: Syntheses of glycosylamino-1,2,3-thiadiazoles and 1,2,4,6-thiatriazine-S-oxide glycosides.

作者：HARUO OGURA、HIROSHI TAKAHASHI、OSAMU SATO

DOI：10.1248/cpb.29.1843

日期：——

The reactions of glycosyl isothiocyanates (1a-c) with diazomethane or ethyl diazoacetate gave the corresponding glycosylamino-1, 2, 3-thiadiazoles (2a-c or 3a, b). Attempted ring transformation of 2 under thermal or basic conditions failed. Similar treatment of D-gluconyl isothiocyanate (1d) with diazomethane afforded D-gluco-pent-1-yl oxathiazolone (5d) in good yield. The reactions of 1a-c with acetoamidine or formamidine hydrochloride under basic conditions gave the corresponding N-glycosyl-N'-acetoamidino-or N-glycosyl-N'-formamidinothiocarboxamides (6a-c ; 7a, c). Subsequent treatment of 6b, c and 7a, c with thionyl chloride under basic conditions afforded the corresponding 1, 2, 4, 6-thiatriazine-S-oxide glycosides (8a-c ; 9a, c) in good yields. Attempted transformation of 8 to 1, 2, 4-triazole glycoside (10) was unsuccessful.

糖基异硫氰酸酯（1a-c）与重氮甲烷或重氮乙酸乙酯反应，得到相应的糖基氨基-1，2，3-噻二唑（2a-c 或 3a，b）。试图在热或碱性条件下对 2 进行环转化的努力失败了。用重氮甲烷对异硫氰酸 D-葡糖基酯（1d）进行类似的处理，可以得到 D-葡糖戊-1-基噁硫唑酮（5d），收率很高。在碱性条件下，1a-c 与乙脒或甲脒盐酸盐反应，得到相应的 N-糖基-N'-乙脒或 N-糖基-N'-甲脒硫代羧酰胺（6a-c；7a，c）。随后，在碱性条件下用亚硫酰氯处理 6b, c 和 7a, c，可以得到相应的 1, 2, 4, 6-噻三嗪-S-氧化物苷（8a-c；9a, c），收率很高。将 8 转化为 1，2，4-三唑苷（10）的尝试没有成功。
Studies on nucleoside analogs. XXI. A convenient synthesis of 1,2,4-triazole-5-thione glycosides.

作者：HARUO OGURA、HIROSHI TAKAHASHI、OSAMU SATO

DOI：10.1248/cpb.29.2188

日期：——

The reaction of glycosyl isothiocyanates (1a-c) with acyl or aroyl hydrazine, followed by treatment with Ac2O-H3PO4, afforded 1, 2, 4-triazole-5-thione glycosides (20a, 21a-c, 22a) in fair yields. Attempts to prepare 1, 2, 4-triazole glycoside analogs with acetic anhydride or sodium methoxide failed. The reaction of glycosyl-2-(phenyl-or pyrid-2-ylhydrazine) thiocarboxamides (6a, 7a) with phosgene in pyridine or triethylamine gave thiadiazole-5-thiones (8a, 9a) instead of 1, 2, 4-triazole glycosides.

糖基异硫氰酸酯 (1a-c) 与酰基或芳酰肼反应，然后用 Ac2O-H3PO4 处理，以良好的收率得到 1,2,4-三唑-5-硫酮糖苷 (20a, 21a-c, 22a)。用乙酸酐或甲醇钠制备1,2,4-三唑糖苷类似物的尝试失败了。糖基-2-(苯基-或吡啶-2-基肼)硫代甲酰胺(6a, 7a)与光气在吡啶或三乙胺中反应生成噻二唑-5-硫酮(8a, 9a)而不是1,2,4-三唑糖苷。