1,2:5,6-二-O-环己亚基-alpha-D-呋喃葡萄糖 | 23397-76-4

• 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: 1,2:5,6-二-O-环己亚基-alpha-D-呋喃葡萄糖
• 中文别名: 1,2:5,6-二-O-亚环己基-Α-D-呋喃葡萄糖；1,2:5,6-二-o-环亚己基-alpha-d-呋喃葡萄糖；1,2:5,6-二-O-环己亚基-α-D-呋喃葡萄糖
• 英文名称: 1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose
• 英文别名: 1,2:5,6-di-O-cyclohexylidene-D-glucofuranose；1,2:5,6-Di-O-cyclohexylidene-a-D-glucofuranose；(3aR,5S,6S,6aR)-5-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]spiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-6-ol
• CAS: 23397-76-4
• 化学式: C₁₈H₂₈O₆
• 分子量: 340.417
• InChiKey: XEYVZLZWQFLSDZ-YIDVYQOGSA-N

物化性质

• 熔点：
  129-135 °C
• 沸点：
  436.21°C (rough estimate)
• 密度：
  1.1440 (rough estimate)
• 稳定性/保质期：

  在常温常压下稳定，应避免接触强氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2932190090
• 安全说明：
  S22,S24/25,S26,S36
• 储存条件：
  存储在阴凉、干燥的地方。

SDS

Name:	1 2:5 6-Di-O-Cyclohexylidene-Alpha-D-Gluco Furanose 96% Material Safety Data Sheet
Synonym:	None known
CAS:	23397-76-4

Section 1 - Chemical Product MSDS Name:1 2:5 6-Di-O-Cyclohexylidene-Alpha-D-Gluco Furanose 96% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
23397-76-4	1,2:5,6-Di-O-Cyclohexylidene-Alpha-D-G	96	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 23397-76-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 130.00 - 134.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C18H28O6
Molecular Weight: 340.41

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 23397-76-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,2:5,6-Di-O-Cyclohexylidene-Alpha-D-Gluco Furanose - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 23397-76-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 23397-76-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 23397-76-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

合成制备方法

用途

反应信息

• 作为反应物：
  描述：

  1,2:5,6-二-O-环己亚基-alpha-D-呋喃葡萄糖 在 吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 双丙酮半乳糖
  参考文献：
  名称：

  Duan, Shaoming; Binkley, Edith R.; Binkley, Roger W., Journal of Carbohydrate Chemistry, 1995, vol. 14, # 7, p. 1029 - 1034

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 1,2:5,6-二-O-环己亚基-alpha-D-呋喃葡萄糖
  参考文献：
  名称：

  Duan, Shaoming; Binkley, Edith R.; Binkley, Roger W., Journal of Carbohydrate Chemistry, 1995, vol. 14, # 7, p. 1029 - 1034

  摘要：

  DOI：

文献信息

• Diastereoselective deprotonative metalation of chiral ferrocene derived acetals and esters using mixed lithium–cadmium and lithium–zinc combinations
  作者：Gandrath Dayaker、Aare Sreeshailam、D. Venkata Ramana、Floris Chevallier、Thierry Roisnel、Shinsuke Komagawa、Ryo Takita、Masanobu Uchiyama、Palakodety Radha Krishna、Florence Mongin

  DOI：10.1016/j.tet.2014.02.010

  日期：2014.3

  derivative in 74% yield with 90% de (SP diastereoisomer) using the base generated from CdCl2 and Li(TMP) (3 equiv), and in 85% yield with 91% de (SP diastereoisomer) through a double asymmetric induction using a chiral lithium–zinc base generated from ZnCl2·TMEDA and lithium (R)-bis(1-phenylethyl)amide (4 equiv). In contrast, using a combination prepared from ZnCl2 and Li(TMP) (4 equiv) with the ferrocene carboxylate

  原位双金属组合，尤其是由MCl 2（TMEDA）（M = Zn，Cd; TMEDA = N，N，N'，N'-四甲基乙二胺）和Li（TMP）（3或4当量，TMP = 2筛选了（2,6,6-四甲基哌啶子基）具有手性基团的非对映选择性去质子化二茂铁的能力。使用由CdCl 2和Li（TMP）（3当量）生成的碱，由双丙酮d-葡萄糖生成的二茂铁羧酸盐以74％的产率提供90％的de（S P非对映异构体）相应的2-碘衍生物。收率91％de（S P非对映异构体）通过使用由ZnCl 2 ·TMEDA和锂（R）-双（1-苯乙基）酰胺（4当量）生成的手性锂锌基双不对称诱导。相比之下，使用由ZnCl 2和Li（TMP）（4当量）制备的组合物与由6-（叔丁氧羰基氨基）-6-脱氧-3- O-甲基-1,2- O-异亚丙基获得的二茂铁羧酸盐-α- d -glucofuranose导致ř P分离之后碘在57％衍生物的产率。在分离的S
• Enantioselective [1,2]-Stevens Rearrangement Using Sugar-Derived Alkoxides as Chiral Promoters
  作者：Katsuhiko Tomooka、Junichiro Sakamaki、Manabu Harada、Ryoji Wada

  DOI：10.1055/s-2008-1032107

  日期：——

  The first example of enantioselective base-induced [1,2]-Stevens rearrangement was achieved by using the newly developed D-glucose-derived lithium alkoxide as a chiral promoter. This rearrangement provides an α-amino ketone having a pseudoquaternary chiral center in an enantioenriched form.

  通过使用新开发的 D-葡萄糖衍生的醇锂作为手性促进剂，实现了对映选择性碱基诱导的 [1,2]-史蒂文斯重排的第一个例子。这种重排提供了具有对映体富集形式的假季铵手性中心的α-氨基酮。
• New carbohydrate-based chiral auxiliaries in Diels–Alder reaction
  作者：Maria L.G. Ferreira、Sergio Pinheiro、Clarissa C. Perrone、Paulo R.R. Costa、Vı́tor F. Ferreira

  DOI：10.1016/s0957-4166(98)00286-9

  日期：1998.8

  The carbohydrate derivatives 1–5 were evaluated as chiral auxiliaries in the Diels–Alder reaction of its acrylate derivatives 6a–e with cyclopentadiene promoted by Lewis acids. Although excellent endo:exo ratios (98:2) were obtained in many cases, the π-facial selectivities were from low to moderate (up to 60% d.e.). An effect of non-coordinating solvents reversing the stereoselectivities of adducts

  碳水化合物衍生物1 - 5评价为在其丙烯酸酯衍生物的Diels-Alder反应的手性助剂6A - ë与环戊二烯由路易斯酸促进。尽管在许多情况下获得了极好的内/外比（98：2），但π面选择性从低到中（高达60％de）。还发现非配位溶剂会逆转由丙烯酸酯6a，b获得的加合物的立体选择性。
• Synthesis of Enantiopure 1-Alkoxyallenes and their 3-Alkylated Derivatives
  作者：Arndt Hausherr、Beate Orschel、Stefan Scherer、Hans-Ulrich Reissig

  DOI：10.1055/s-2001-15225

  日期：——

  A series of enantiopure 1-alkoxyallenes 1a-1f was prepared starting from propargyl bromide and the corresponding optically active alcohols via propargyl ethers 3a-3f as intermediates. In addition, disubstituted enantiopure allene derivatives 5a-5c were synthesized by isomerization of the corresponding alkynes 4a-4c. Allene derivative 5a was also prepared via an alternative route with 1-trimethylsilylallene derivative 6a as crucial intermediate.

  一系列手性纯的1-烷氧基丙二烯1a-1f，通过从炔丙基溴和相应的手性醇出发，经由炔丙基醚3a-3f作为中间体而制备得到。此外，通过相应炔烃4a-4c的异构化反应，合成了二取代的手性纯丙二烯衍生物5a-5c。丙二烯衍生物5a还通过另一条途径合成，其中1-三甲基硅基丙二烯衍生物6a作为关键中间体。
• ASYMMETRIC INDUCTION IN THE REACTION OF NONSYMMETRICAL PHOSPHINIC AND PHOSPHINOUS ACID CLORIDES WITH DERIVATIVES OF D-GLUCOFURANOSE
  作者：Oleg I. Kolodiazhnyi、Evgen V. Grishkun

  DOI：10.1080/10426509608037959

  日期：1996.8.1

  Abstract Reaction of nonsymmetrically substituted chlorophosphines (1–3) with (−)-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose (1) or (−)-1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose (5) proceeds with high stereoselectivity to give stereochemically pure phosphinic acid esters (6–8), which are starting compounds for the preparation of chiral organophosphorus compounds. Reaction of benzyl-phenylphosphinous

  摘要 非对称取代的氯膦 (1–3) 与 (-)-1,2:3,5-二-O-异亚丙基-α-D-呋喃葡萄糖 (1) 或 (-)-1,2:5,6 的反应-二-O-亚环己基-α-D-呋喃葡萄糖（5）具有高立体选择性，得到立体化学纯的次膦酸酯（6-8），这是制备手性有机磷化合物的起始化合物。苄基-苯基次膦酰氯与(1)的反应产生光学纯的次膦酸酯(9)。根据碱的性质、溶剂、温度和氯膦过量来研究反应的立体化学。