1,2-O-cyclohexylidene-3-O-methyl-α-D-glucofuranose | 13322-87-7

• 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
• 英文名称: 1,2-O-cyclohexylidene-3-O-methyl-α-D-glucofuranose
• 英文别名: 1,2-O-cyclohexyliden-3-O-methyl-α-D-glucofuranose；1,2-O-Cyclohexylidene-3-O-methyl-alpha-D-glucofuranose；(1R)-1-[(3aR,5R,6S,6aR)-6-methoxyspiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-5-yl]ethane-1,2-diol
• CAS: 13322-87-7
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: GWIJXRQWFMLKAN-RMPHRYRLSA-N

物化性质

• 熔点：
  98-102 °C
• 沸点：
  377.3°C (rough estimate)
• 密度：
  1.2106 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 海关编码：
  29400090
• 安全说明：
  S24/25

SDS

Name:	1 2-O-Cyclohexylidene-3-O-Methyl-Alpha-D-Glucofuranose 98% Material Safety Data Sheet
Synonym:	None Known
CAS:	13322-87-7

Section 1 - Chemical Product MSDS Name:1 2-O-Cyclohexylidene-3-O-Methyl-Alpha-D-Glucofuranose 98% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13322-87-7	1,2-O-Cyclohexylidene-3-O-Methyl-Alpha	98%	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. Runoff from fire control or dilution water may cause pollution.
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:
Keep container closed when not in use. 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# 13322-87-7: 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 minimize contact with skin.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 98.00 - 101.00 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: C13H22O6
Molecular Weight: 274.30

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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# 13322-87-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,2-O-Cyclohexylidene-3-O-Methyl-Alpha-D-Glucofuranose - 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.
WGK (Water Danger/Protection)
CAS# 13322-87-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13322-87-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13322-87-7 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

反应信息

• 作为反应物：
  描述：

  1,2-O-cyclohexylidene-3-O-methyl-α-D-glucofuranose 在 四丁基氯化铵 、 苄基三丁基氯化铵 barium hydroxide octahydrate 、 sodium carbonate 、 calcium carbonate 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 1,2-O-cyclohexylidene-3-O-methyl-5,6-anhydro-α-L-glucofuranose
  参考文献：
  名称：

  Zhdanov, Yu. A.; Alekseev, Yu. E.; Alekseeva, V. G., Journal of general chemistry of the USSR, 1988, vol. 58, # 11, p. 2325 - 2329

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2:5,6-二-O-环亚己基-3-O-甲基-Alpha-D-呋喃葡萄糖 在 氢氧化钾 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以55%的产率得到1,2-O-cyclohexylidene-3-O-methyl-α-D-glucofuranose
  参考文献：
  名称：

  O-Hetaryl substituted carbohydrates and their neurotropic activity

  摘要：

  DOI：

  10.1007/bf00767389

文献信息

• The Prediction of the Absolute Stereochemistry of Primary and Secondary 1,2-Diols by1H NMR Spectroscopy: Principles and Applications
  作者：Félix Freire、José M. Seco、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1002/chem.200500181

  日期：2005.9.19

  absolute configuration of 1,2-diols formed by a primary and a secondary (chiral) hydroxyl group can be deduced by comparison of the 1H NMR spectra of the corresponding (R)- and bis-(S)-MPA esters (MPA = methoxyphenylacetic acid). This method involves the use of the chemical shifts of substituents L1/L2 attached to the secondary (chiral) carbon, and of the hydrogen atom linked to the chiral center (C

  由伯和仲（手性）羟基形成的1,2-二醇的绝对构型可以通过比较相应的（R）-和双-（S）-MPA酯的1H NMR光谱推导得出（MPA =甲氧基苯基乙酸）。该方法涉及使用与仲（手性）碳相连的取代基L1 / L2的化学位移和与手性中心（C alpha-H）相连的氢原子的化学位移作为诊断信号。理论（AM1，HF和B3 LYP计算）和实验数据（动态和低温NMR光谱，氘代衍生物研究，恒定耦合分析，圆二色性（CD）光谱以及使用许多已知绝对二醇的NMR研究）构型）证明为那些信号获得的delta delta（RS）的符号与二醇的绝对构型相关。
• Chiral 1,2-Diols: The Assignment of Their Absolute Configuration by NMR Made Easy
  作者：Félix Freire、José Manuel Seco、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1021/ol9021639

  日期：2010.1.15

  The absolute configuration of a 1,2-primary/secondary diol can be easily determined by preparation of its bis-(R)- and bis-(S)-9-AMA ester derivatives, followed by comparison of the NMR chemical shifts of the diastereotopic methylene protons in the two derivatives. Alternatively, the assignment can be carried out using only one derivative if the evolution with temperature of the signals corresponding

  通过制备双（R）-和双（S）-9-AMA酯衍生物，然后比较NMR的NMR化学位移，可以轻松确定1,2-伯/仲二醇的绝对构型。非对位亚甲基质子中的两个衍生物。或者，如果分析了与CαH质子相对应的信号随温度的演变，则可以仅使用一种导数进行赋值。
• Suryawanshi, S.N.; Rani, A.; Bhakuni, D.S., Synthetic Communications, 1990, vol. 20, # 5, p. 625 - 632
  作者：Suryawanshi, S.N.、Rani, A.、Bhakuni, D.S.

  DOI：——

  日期：——
• Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols:  Scope and Mechanistic Insight
  作者：Michael J. Martinelli、Rajappa Vaidyanathan、Joseph M. Pawlak、Naresh K. Nayyar、Ulhas P. Dhokte、Christopher W. Doecke、Lisa M. H. Zollars、Eric D. Moher、Vien Van Khau、Berta Košmrlj

  DOI：10.1021/ja016031r

  日期：2002.4.1

  This paper describes a convenient protocol for the regioselective sulfonylation of alpha-chelatable alcohols. Typically, the reaction of alpha-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of Sn-119 NMR studies.
• Facile Access to Novel [60]Fullerenyl Diethers and [60]Fullerene–Sugar Conjugates via Annulation of Diol Moieties
  作者：Wen-Qiang Zhai、Sheng-Peng Jiang、Ru-Fang Peng、Bo Jin、Guan-Wu Wang

  DOI：10.1021/acs.orglett.5b00536

  日期：2015.4.17

  A general and facile annulation of various diol motifs to [60]fullerene has been developed. This protocol can afford not only 6- to 10-membered-ring fullerenyl diethers in one step from simple acyclic diols but also directly couple [60]fullerene with a variety of structurally diverse sugars. The [60]fullerene-sugar conjugates formed do not require any linker moiety and maintain their inherent structural integrity. The electrochemistry of the fullerenyl diethers and [60]fullerene-sugar conjugates has also been investigated.