3-O-乙酰基-1,2:5,6-二-O-异丙基-Alpha-D-呋喃(型)葡萄糖 | 16713-80-7

• 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
• 中文名称: 3-O-乙酰基-1,2:5,6-二-O-异丙基-Alpha-D-呋喃(型)葡萄糖
• 中文别名: 3-O-乙酰基-1,2:5,6-二-O-异丙基-Α-D-呋喃(型)葡萄糖；3-O-乙酰基-1,2:5,6-二-O-异丙基-α-D-呋喃(型)葡萄糖
• 英文名称: 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose
• 英文别名: 3-O-Acetyl-1,2:5,6-di-O-isopropyliden-α-D-glucofuranose；3-O-Acetyl-1,2:5,6-DI-O-isopropylidene-alpha-D-glucofuranose；[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 16713-80-7
• 化学式: C₁₄H₂₂O₇
• 分子量: 302.324
• InChiKey: QZKDRLZSJSWQPS-RMPHRYRLSA-N

物化性质

• 熔点：
  60-62 °C(lit.)
• 比旋光度：
  -37°(c=1,CHCl3,25℃)
• 沸点：
  403.35°C (rough estimate)
• 密度：
  1.2585 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  2
• RTECS号：
  LZ4910000
• 海关编码：
  29389090
• 安全说明：
  S24/25
• 储存条件：
  0-6°C

SDS

Name:	3-O-Acetyl-1 2:5 6-Di-O-Isopropylidene-Alpha-D-Glucofuranose 98% Material Safety Data Sheet
Synonym:	1,2:5,6-Bis-O-(1-Methylethylidene)-Alpha-D-glucofuranose Acetate
CAS:	16713-80-7

Section 1 - Chemical Product MSDS Name:3-O-Acetyl-1 2:5 6-Di-O-Isopropylidene-Alpha-D-Glucofuranose 98% Material Safety Data Sheet
Synonym:1,2:5,6-Bis-O-(1-Methylethylidene)-Alpha-D-glucofuranose Acetate

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16713-80-7	3-O-Acetyl-1,2:5,6-Di-O-Isopropylidene	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. Wash mouth out with 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. 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. Keep refrigerated. (Store below 4C/39F.)

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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# 16713-80-7: 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 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: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 60 - 62 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: slightly soluble
Specific Gravity/Density:
Molecular Formula: C14H22O7
Molecular Weight: 302.1498

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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.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16713-80-7: LZ4910000 LD50/LC50:
CAS# 16713-80-7: Oral, mouse: LD50 = >4 gm/kg.
Carcinogenicity:
3-O-Acetyl-1,2:5,6-Di-O-Isopropylidene-Alpha-D- Glucofuranose - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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# 16713-80-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16713-80-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16713-80-7 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：

  3-O-乙酰基-1,2:5,6-二-O-异丙基-Alpha-D-呋喃(型)葡萄糖 在 二叔丁基过氧化物 、 三苯基硅烷 作用下， 反应 12.0h， 以66%的产率得到3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside
  参考文献：
  名称：

  A Novel Method for the Deoxygenation of Acetylated Sugars

  摘要：

  据报道，在均聚条件下，乙酰化的外科胂 1 在三苯基硅烷的作用下转化为脱氧糖 2。带有乙酰化伯醇或仲醇的呋喃糖和吡喃糖都能有效地脱氧。

  DOI：

  10.1055/s-1988-27593
• 作为产物：
  描述：

  3-O-[(t-butyl)dimethylsilyl]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 potassium fluoride 、 N-(methylpolystyrene)-4-(methylamino)pyridine 、 四丁基溴化铵 作用下， 以 水 、 乙腈 为溶剂， 反应 0.28h， 生成 3-O-乙酰基-1,2:5,6-二-O-异丙基-Alpha-D-呋喃(型)葡萄糖
  参考文献：
  名称：

  RAPID CARBOHYDRATE PROTECTING GROUP MANIPULATIONS ASSISTED BY MICROWAVE DIELECTRIC HEATING

  摘要：

  The protocols for oligosaccharide synthesis are often tedious due to extended synthetic routes and reaction times. We herein describe methods assisted by microwave dielectric heating, which enable very short reaction times and high yields for the introduction and removal of eleven of the most commonly used protecting groups in carbohydrate syntheses. Several examples are reported, where solid supported reagents in combination with microwave dielectric heating have been used. This results in both faster and easier synthesis and purification.

  DOI：

  10.1081/car-100105712

文献信息

• Quantitation of Monosaccharide Isotopic Enrichment in Physiologic Fluids by Electron Ionization or Negative Chemical Ionization GC/MS Using Di-<i>O</i>-isopropylidene Derivatives
  作者：David L. Hachey、W. Reed Parsons、Siripoom McKay、Morey W. Haymond

  DOI：10.1021/ac990724x

  日期：1999.10.1

  The aldonitrile pentaacetate and other derivatives lack ions in the electron ionization (EI) spectra possessing an intact hexose structure and thus must be analyzed by chemical ionization GC/MS in order to study multiple isotopomers. We report methods for quantitation of hexose di-O-isopropylidene acetate (IPAc) or pentafluorobenzoyl (PFBz) esters. These were prepared in a two-step procedure using inexpensive reagents that do not adversely impact the isotopomer structure of the sugar. The acetate derivative possesses an abundant [M − CH3] ion in the EI spectrum which is suitable for quantitative analysis of isotopomers. The negative chemical ionization (NCI) spectrum of the corresponding pentafluorobenzoyl derivative has a dominant molecular anion. Moreover, the PFBz derivative is about 100-fold more sensitive than the acetate, which offers some advantages for analysis of minor hexoses found in plasma. Isotopic calibration curves of [U-13C]glucose are linear over the 0.1−60% tracer/tracee range tested. The useful range for isotopic tracer studies is 25−2500 pmol for EI analysis of the acetate derivative and 0.1−55 pmol for NCI analysis of PFBz derivative (sample amount injected). For most studies where sample size is not limited, EI-GC/MS analysis of the IPAc derivative is preferred. NCI-GC/MS analysis is reserved when sample size is limiting or when studies involve hexoses other than glucose that are normally present at low concentration.

  aldonitrile pentaacetate和其他具有完整己糖结构的衍生物在电子离子化（EI）光谱中缺乏离子，因此必须通过化学离子化GC/MS分析才能研究多种同位素异构体。我们报告了己糖二-O-异丙叉乙酸酯（IPAc）或五氟苯甲酰（PFBz）酯的定量方法。这些是通过使用廉价试剂的两步程序制备的，这些试剂不会对糖的同位素结构产生不利影响。乙酸酯衍生物在EI光谱中具有丰富的[M - CH3]离子，适合用于同位素异构体的定量分析。相应的五氟苯甲酰衍生物的负化学离子化（NCI）光谱具有主导的分子阴离子。此外，PFBz衍生物的灵敏度大约是乙酸酯的100倍，这为分析在血浆中发现的次要己糖提供了一些优势。[U-13C]葡萄糖的同位素校准曲线在测试的0.1-60%示踪剂/本体范围内是线性的。同位素示踪剂研究的有用范围是25-2500 pmol用于乙酸酯衍生物的EI分析，0.1-55 pmol用于PFBz衍生物的NCI分析（注射的样品量）。对于大多数样本大小不受限制的研究，优先选择IPAc衍生物的EI-GC/MS分析。当样本大小受限或研究涉及通常以低浓度存在的非葡萄糖己糖时，保留NCI-GC/MS分析。
• Me₃SI-promoted chemoselective deacetylation: a general and mild protocol
  作者：Aakanksha Gurawa、Manoj Kumar、Sudhir Kashyap

  DOI：10.1039/d1ra03209g

  日期：——

  Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developed via employing KMnO4 as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses

  通过使用 KMnO4 作为添加剂，开发了一种 Me3SI 介导的简单而有效的乙酰基化学选择性脱保护方案。这种化学选择性脱乙酰化适用于多种底物，可耐受碳水化合物、氨基酸、天然产物、杂环化合物和一般支架中的多种敏感官能团。该协议很有吸引力，因为它使用环境友好的试剂系统在环境条件下进行定量和清洁转化。
• Transacetalation: a convenient, nonaqueous method for effecting the deprotection of isopropylidene and benzylidene derivatives of sugars
  作者：Mark A. Andrews、George L. Gould

  DOI：10.1016/s0008-6215(00)90486-5

  日期：1992.5

  Abstract Sugar isopropylidene and benzylidene derivatives can be readily deprotected under nonaqueous conditions by treatment of a dichloromethane solution of the protected sugar with an excess of a sacrificial glycol in the presence of a catalytic amount of p -toluenesulfonic acid. The reaction is conveniently monitored by GLC, and the fully or partially deprotected product precipitates from solution

  摘要在催化量的对甲苯磺酸存在下，用过量的牺牲二醇处理被保护糖的二氯甲烷溶液，可以在非水条件下容易地将糖异亚丙基和亚苄基衍生物去保护。通过GLC方便地监测反应，并且完全或部分脱保护的产物从溶液中沉淀出来。
• Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols
  作者：Robert S.L. Chapman、Molly Francis、Ruth Lawrence、Joshua D. Tibbetts、Steven D. Bull

  DOI：10.1016/j.tet.2018.09.014

  日期：2018.11

  Formyloxyacetoxyphenylmethane, symmetric 1,1-diacylals and mixed 1-pivaloxy-1-acyloxy-1-phenylmethanes have been used as moisture stable O-formylating and O-acylating reagents for primary and secondary alcohols, allylic alcohols and phenols under solvent/catalyst free conditions to afford their corresponding esters in good yield.

  在无溶剂/催化剂的情况下，甲氧基乙氧基苯基甲烷，对称的1,1-二醛和混合的1-新戊氧基-1-酰氧基-1-苯基甲烷已被用作伯，仲醇，烯丙基醇和苯酚的湿气稳定的O-甲酰化和O-酰化试剂。条件以高收率得到其相应的酯。
• Iodine: A versatile reagent in carbohydrate chemistry IV. Per-O-acetylation, regioselective acylation and acetolysis
  作者：K.P.Ravindranathan Kartha、Robert A. Field

  DOI：10.1016/s0040-4020(97)00742-4

  日期：1997.8

  acid for promoting the per-O-acetylation of unprotected sugars. Under controlled conditions it can bring about regioselective acylation of carbohydrate derivatives. At higher concentration and with longer reaction times, iodine can effect the selective acetolysis of benzyl ether-protected primary hydroxyl groups. All of these reactions proceed in high yield, are easy to carry out and make use of readily

  已经发现碘是用于促进未保护的糖的过-O-乙酰化的有效的路易斯酸。在受控条件下，它可以引起碳水化合物衍生物的区域选择性酰化。在更高的浓度和更长的反应时间下，碘会影响苄基醚保护的伯羟基的选择性乙酰水解。所有这些反应均以高收率进行，易于进行，并利用廉价且易于处理的碘。