对硝基苯基-alpha-L-吡喃鼠李糖苷 | 18918-31-5

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 对硝基苯基-alpha-L-吡喃鼠李糖苷
• 中文别名: 4-硝基苯基-Α-L-吡喃鼠李糖苷；对硝基苯基-alpha-L-鼠李糖苷
• 英文名称: p-nitrophenyl α-L-rhamnopyranoside
• 英文别名: 4-Nitrophenylrhamnoside；(2S,3R,4R,5R,6S)-2-methyl-6-(4-nitrophenoxy)oxane-3,4,5-triol
• CAS: 18918-31-5
• 化学式: C₁₂H₁₅NO₇
• 分子量: 285.254
• InChiKey: YILIDCGSXCGACV-UOAXWKJLSA-N

物化性质

• 熔点：
  179°C
• 沸点：
  515.4±50.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：20mg/mL； DMSO：15mg/mL；乙醇：0.25mg/mL； PBS（pH 7.2）：2 mg/mL
• LogP：
  1.170 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 海关编码：
  29400090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319
• 储存条件：
  -20°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-Nitrophenyl α-L-rhamnopyranoside
CAS-No. : 18918-31-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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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

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: p-Nitrophenyl 6-deoxy-α-L-mannopyranoside
Synonyms
Formula : C12H15NO7
Molecular Weight : 285,25 g/mol

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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

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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)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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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.

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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.
Recommended storage temperature: -20 °C
Specific end uses
no data available

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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).

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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

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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

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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

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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

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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.

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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

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

4-硝基苯基α-L-鼠李吡喃糖苷是一种鼠李糖，可以作为鼠李糖苷酶的底物。

反应信息

• 作为反应物：
  描述：

  对硝基苯基-alpha-L-吡喃鼠李糖苷 在 甲醇 、 Pd-BaSO₄ 作用下， 生成 1-(4-aminophenoxy)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Westphal; Feier, Chemische Berichte, 1956, vol. 89, p. 582,587

  摘要：

  DOI：
• 作为产物：
  描述：

  p-nitrophenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 对硝基苯基-alpha-L-吡喃鼠李糖苷
  参考文献：
  名称：

  Westphal; Feier, Chemische Berichte, 1956, vol. 89, p. 582,587

  摘要：

  DOI：

文献信息

• Synthesis of allyl and benzyl 4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-2,3-di-O-methyl-α-l-rhamnopyranoside
  作者：Jose R. Mariño-Albernas、Vicente Verez-Bencomo、Leandro Gonzalez、Carlos S. Perez

  DOI：10.1016/0008-6215(87)80099-x

  日期：1987.8

  Abstract Condensation of 2,4-di- O -acetyl-3,6-di- O -methyl-α- d -glucopyranosyl bromide with either allyl or benzyl 2,4-di- O -methyl-α- l -rhamnopyranoside in the presence of mercuric cyanide, followed by O -deacetylation, gave the title oligosaccharides in excellent yields.

  摘要2,4-二-O-乙酰基-3,6-二-O-甲基-α-d-吡喃葡萄糖基溴化物与烯丙基或苄基的2,4-二-O-甲基-α-1-鼠李糖吡喃糖苷缩合。氰化汞的存在，然后进行O-脱乙酰基反应，可以极好的收率得到标题寡糖。
• Creation of an α-Mannosynthase from a Broad Glycosidase Scaffold
  作者：Keisuke Yamamoto、Benjamin G. Davis

  DOI：10.1002/anie.201201081

  日期：2012.7.23

  α‐Mannosides made easy: Mutation of a family‐GH31 α‐glucosidase that displays plasticity to alterations at the 2‐OH position of donor substrates created an efficient α‐mannoside‐synthesizing biocatalyst. A simple fluoride donor reagent was used for the synthesis of a range of mono‐α‐mannosylated conjugates using the α‐mannosynthase displaying low (unwanted) oligomerization activity.

  α-甘露糖苷变得容易：GH31 α-葡萄糖苷酶家族的突变对供体底物的 2-OH 位置的改变显示出可塑性，创造了一种有效的 α-甘露糖苷合成生物催化剂。使用显示低（不需要的）寡聚化活性的 α-甘露糖合酶，将一种简单的氟化物供体试剂用于合成一系列单-α-甘露糖基化偶联物。
• Sugar-modified cytostatics
  申请人：Bayer Aktiengesellschaft

  公开号：US06271342B1

  公开（公告）日：2001-08-07

  The invention relates to cytostatics which, by modification with sugar, are tumor-specific. Suitable spacers ensure serum stability and at the same time an intracellular action.

  这项发明涉及通过与糖类改性的细胞毒药物，这些药物具有肿瘤特异性。合适的间隔物确保血清稳定性，同时也保证细胞内作用。
• Regioselective Galactofuranosylation for the Synthesis of Disaccharide Patterns Found in Pathogenic Microorganisms
  作者：Laurent Legentil、Yari Cabezas、Olivier Tasseau、Charles Tellier、Franck Daligault、Vincent Ferrières

  DOI：10.1021/acs.joc.7b00565

  日期：2017.7.21

  Koenigs–Knorr glycosylation of acceptors with more than one free hydroxyl group by 2,3,5,6-tetrabenzoyl galactofuranosyl bromide was performed using diphenylborinic acid 2-aminoethyl ester (DPBA) as inducer of regioselectivity. High regioselectivity for the glycosylation on the equatorial hydroxyl group of the acceptor was obtained thanks to the transient formation of a borinate adduct of the corresponding

  使用二苯基硼酸2-氨基乙基酯（DPBA）作为区域选择性的诱导剂，进行了2,3,5,6-四苯甲酰半乳糖呋喃糖基溴的带有多个游离羟基的受体的Koenigs-Knorr糖基化反应。由于相应的1，2-顺式二醇的硼酸酯加合物的瞬时形成，获得了在受体的赤道羟基上的糖基化的高区域选择性。然而，原酸酯副产物的形成妨碍了该方法的效率。有趣的是，受体的O -6或C -1上的吸电子基团使反应发生位移，有利于所需的含半呋喃呋喃糖基的二糖。对于p的呋喃糖基化获得了最佳产率-硝基苯基6- O-乙酰基甘露吡喃糖苷。在某些病原体的糖杯中发现的其他二糖的前体是根据相同的方法合成的，收率范围为45％至86％。这是合成生物学相关糖缀合物的良好选择。
• Synthesis of aryl α-<i>O-</i>L-rhamnopyranoside by two-step reaction in one pot
  作者：Nianping Liu、Xiangguang Tian、Zekun Ding、Yongda Zhou、Wan Zhang、Qingbing Wang、Yi Zhang、Yijun Gu、Jianbo Zhang

  DOI：10.1080/07328303.2017.1390578

  日期：2017.6.13

  approach in two steps and one pot using the rhamnopyranosyl chloride as key intermediate. The two-step one-pot procedure is more convenient and environmentally friendly, compared to the published synthetic routes. Besides, the structure-reactivity relationship and the plausible mechanism for this base-catalyzed glycosylation were discussed by means of the Hammett equation.

  图形摘要摘要使用鼠李糖吡喃糖基氯为主要中间体，通过两步一锅的相转移催化方法方便地合成了标题化合物。与公开的合成路线相比，两步一锅法更方便，更环保。此外，利用Hammett方程讨论了该碱催化的糖基化反应的结构-反应关系和合理的机理。