α-D(+)-五乙酰葡萄糖 | 604-68-2

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: α-D(+)-五乙酰葡萄糖
• 中文别名: a-D-葡糖五乙酸酯；α-五乙酰葡萄糖；1,2,3,4,6-五-O-乙酰-α-D-吡喃葡萄糖；1,2,3,4,6-五乙酰-α-D-吡喃葡萄糖酯；α-D-葡萄糖五乙酸酯；1,2,3,4,6-alpha-D-葡萄糖五乙酸酯；五-O-乙酰-α-D-吡喃葡萄糖；α-D-葡糖五乙酸酯；葡萄糖五乙酸酯；α-葡萄糖五乙酸酯；1,2,3,4,6-α-D-葡萄糖五乙酸酯；Α-D-葡萄糖五乙酸酯；Α-D-葡萄糖乙酸酯；Α-D-葡糖五乙酸酯；1,2,3,4,6-O-五乙酰基-Α-D-葡萄糖；ALPHA-D-葡萄糖五乙酸酯；1,2,3,4,6-五-O-乙酰基-Α-D-吡喃葡萄糖；Α-D-五乙酰基葡萄糖；五乙酸-2,3,4,5,6-葡萄糖酯；2,3,4,5,6-alpha-D-葡萄糖五乙酸酯
• 英文名称: α-D-glucopyranose peracetylate
• 英文别名: α-D-glucopyranose pentaacetate；1,2,3,4,6-penta-O-acetyl-α-D-glucopyranose；α-D-glucose pentaacetate；1,2,3,4,6-penta-O-acetyl-α-D-glucopyranoside；1,2,3,4,6-penta-O-acetyl-D-glucopyranoside；(2R,3R,4S,5R,6R)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate；penta-O-acetyl-α-D-glucopyranose；β-D-glucose pentaacetate；D-(+)-glucose pentaacetate；alpha-D-Glucose pentaacetate；[(2R,3R,4S,5R,6R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate
• CAS: 604-68-2
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: LPTITAGPBXDDGR-LJIZCISZSA-N

物化性质

• 熔点：
  111-113 °C
• 比旋光度：
  97 º (c=1, CHCl3)
• 沸点：
  435.58°C (rough estimate)
• 密度：
  1.3984 (rough estimate)
• 溶解度：
  氯仿：0.1 g/mL，澄清，无色
• LogP：
  1.87 at 25℃ and pH5.7
• 保留指数：
  2257;2257
• 稳定性/保质期：
  性质与稳定性： 常温常压下，该物质不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xn,Xi
• 安全说明：
  S24/25
• 危险类别码：
  R21
• WGK Germany：
  3
• 海关编码：
  29400000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  贮存： 将密器密封后，放入密封的主容器中，并存放于阴凉、干燥的地方。

SDS

Name:	alpha-D-Glucose pentaacetate 98% Material Safety Data Sheet
Synonym:	1,2,3,4,6-Pentaacetyl-alpha-D-glucos
CAS:	604-68-2

Section 1 - Chemical Product MSDS Name:alpha-D-Glucose pentaacetate 98% Material Safety Data Sheet
Synonym:1,2,3,4,6-Pentaacetyl-alpha-D-glucos

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
604-68-2	alpha-D-Glucose pentaacetate	98	210-073-2

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.
Expected to be a low ingestion hazard.
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. If irritation develops, get medical aid.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. 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 if cough or other symptoms appear.
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:
Do NOT use water directly on fire. Use water spray to cool fire-exposed containers. 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. Avoid breathing dust, vapor, mist, or gas. 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# 604-68-2: 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 powder
Odor: Odorless
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 111 - 112 deg C
Autoignition Temperature: > 500 deg C (> 932.00 deg F)
Flash Point: > 150 deg C (> 302.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: >200 deg C
Solubility in water: < 5 G/L (25C)
Specific Gravity/Density:
Molecular Formula: C16H22O11
Molecular Weight: 390.33

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat.
Incompatibilities with Other Materials:
Strong 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# 604-68-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
alpha-D-Glucose pentaacetate - 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# 604-68-2: No information available.
Canada
CAS# 604-68-2 is listed on Canada's NDSL List.
CAS# 604-68-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 604-68-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：主要应用于生化反应，并作为医药中间体等。

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
  β-D-葡萄糖五乙酸酯	β-D-glucose pentaacetate	604-69-3	C16H22O11	390.344
  2,3,4,6-四-o-乙酰基-alpha-d-吡喃葡萄糖苷甲酯	Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester	604-70-6	C15H22O10	362.334
  1,6-脱水-β-D-葡萄糖-2,3,4-三邻醋酸	2,3,4-tri-O-acetyllevoglucosan	13242-55-2	C12H16O8	288.254
  ——	2,3,4,6-tetraacetylglucose	——	C14H20O10	348.307
  ——	Benzyl-2,3-O-isopropyliden-5-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-ribofuranosid	78416-55-4	C29H38O14	610.612
  甲基 Β-D-吡喃葡萄糖苷	methyl beta-D-glucopyranoside	709-50-2	C7H14O6	194.185
  alpha-甲基葡萄糖甙	methyl-alpha-D-glucopyranoside	97-30-3	C7H14O6	194.185
  ——	tetra-acetyl glucosamine	26108-75-8	C14H21NO9	347.322
  D-(+)-松三糖水合物	melezitose	597-12-6	C18H32O16	504.442
  1,6-脱水-β-D-葡萄糖	levoglucosan	498-07-7	C6H10O5	162.142
• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  β-D-葡萄糖五乙酸酯	β-D-glucose pentaacetate	604-69-3	C16H22O11	390.344
  1,2,3,6-四-o-乙酰基-alpha-d-吡喃葡萄糖	1,2,3,6-tetra-O-acetyl-α-D-glucopyranose	55286-97-0	C14H20O10	348.307
  1,6-脱水-β-D-葡萄糖-2,3,4-三邻醋酸	2,3,4-tri-O-acetyllevoglucosan	13242-55-2	C12H16O8	288.254
  ——	2,3,4,6-tetraacetylglucose	——	C14H20O10	348.307
  ——	2,3,4,5-tetra-O-acetyl-D-glucopyranose	——	C14H20O10	348.307
  2,3,4,6-四-O-乙酰-β-D-吡喃葡萄糖	2,3,4,6-tetra-O-acetyl-β-D-glucopyranose	3947-62-4	C14H20O10	348.307
  2-炔丙基-四-O-乙酰基-β-D-吡喃葡萄糖苷	1-O-propargyl 2,3,4,6-tetra-O-acetyl-β-D-glucose	34272-02-1	C17H22O10	386.356
  ——	geranoiol 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside	84534-34-9	C24H36O10	484.544
  ——	2-isopropyl-5-methylcyclohexyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside	16124-23-5	C24H38O10	486.56
  ——	2-phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside	——	C22H28O10	452.458

反应信息

• 作为反应物：
  描述：

  α-D(+)-五乙酰葡萄糖 在 甲醇 、 calcium sulfate 、 氢溴酸 、 sodium methylate 、 溶剂黄146 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 17.0h， 生成 2-(trimethylsilyl)ethyl β-D-glucopyranoside
  参考文献：
  名称：

  [EN] CONJUGATES OF A PHARMACEUTICAL AGENT AND A MOIETY CAPABLE OF BINDING TO A GLUCOSE SENSING PROTEIN
  [FR] CONJUGUÉS CONSTITUÉS D'UN AGENT PHARMACEUTIQUE ET D'UNE FRACTION APTE SE LIER À UNE PROTÉINE DE DÉTECTION DU GLUCOSE

  摘要：

  这项发明描述了一种新型的配方(I)的药物代理和一种能够结合到葡萄糖感应蛋白的基团的结合物，允许根据葡萄糖浓度可逆释放药物代理。

  公开号：

  WO2017207754A1
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl β-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 草酰氯 、 4 A molecular sieve 、 三氟化硼乙醚 、 四乙基溴化铵 、 氢气 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 130.0 ℃ 、101.33 kPa 条件下， 反应 79.0h， 生成 α-D(+)-五乙酰葡萄糖
  参考文献：
  名称：

  2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

  摘要：

  DOI：

  10.1021/jo00259a006

文献信息

• HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS
  申请人：Academia Sinica

  公开号：US20160102116A1

  公开（公告）日：2016-04-14

  Glycosphingolipids (GSLs) compositions and methods for iNKT-independent induction of chemokines are disclosed.

  糖脂类脂质（GSLs）的组成和诱导化学因子独立于iNKT的方法被揭示。
• Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines
  作者：Asit K. Chakraborti、Rajesh Gulhane

  DOI：10.1039/b304178f

  日期：——

  Perchloric acid adsorbed on silica gel efficiently catalyses acetylation of structurally diverse phenols, alcohols, thiols, and amines under solvent free conditions.

  在无溶剂条件下，吸附在硅胶上的高氯酸可有效催化结构多样的酚，醇，硫醇和胺的乙酰化。
• 喜树碱糖类衍生物及其制备方法与应用
  申请人：广州中医药大学（广州中医药研究院）

  公开号：CN110372766A

  公开（公告）日：2019-10-25

  本发明涉及喜树碱糖类衍生物及其制备方法与应用，属于生物医药领域。本发明喜树碱糖类衍生物的结构式如下述式(I)所示。本发明喜树碱糖类衍生物能明显增加喜树碱与10‑羟基喜树碱的稳定性和水溶性，对不同肿瘤细胞具有不同敏感性。尤其当上述链接链n＝1时，本发明喜树碱糖类衍生物能明显增加对肿瘤细胞的选择性。
• Erbium(III) Triflate as an Extremely Active Acylation Catalyst
  作者：Antonio Procopio、Renato Dalpozzo、Antonio De?Nino、Loredana Maiuolo、Beatrice Russo、Giovanni Sindona

  DOI：10.1002/adsc.200404132

  日期：2004.10

  Erbium(III) triflate is a powerful catalyst for the acylation of alcohols and phenols. The reaction works well for a large variety of simple and functionalized substrates by using different kinds of acidic anhydrides Ac2O, (EtCO)2O, [(CH3)3CO]2O, Bz2O, and (CF3CO)2O} without isomerisation of chiral centres. Moreover, the catalyst can be easily recycled and reused without significant loss of activity

  三氟甲磺酸（（III）是醇和苯酚酰化的有力催化剂。通过使用不同种类的酸酐Ac 2 O，（EtCO）2 O，[（CH 3）3 CO] 2 O，Bz 2 O，和（CF 3 CO）2 O}，而没有手性中心的异构化。而且，该催化剂可以容易地再循环和再利用而没有明显的活性损失。
• Inhibition of Mitosis by Glycopeptide Dendrimer Conjugates of Colchicine
  作者：David Lagnoux、Tamis Darbre、M. Lienhard Schmitz、Jean-Louis Reymond

  DOI：10.1002/chem.200401294

  日期：2005.6.20

  devices for colchicine. Colchicine was attached to the dendrimers at the cysteine thiol group through a disulfide or thioether linkage. The biological activities of the glycopeptide dendrimer conjugates were evaluated in HeLa tumor cells and non-transformed mouse embryonic fibroblasts (MEFs). The concentrations of glycopeptide dendrimer drug conjugates required to achieve inhibition of cell proliferation

  已经制备了糖肽树状聚合物，其表面上带有四个或八个相同的糖苷部分（β-葡萄糖，α-半乳糖，α-N-乙酰基半乳糖或乳糖），分支内的天然氨基酸（Ser，Thr，His，Asp ，Glu，Leu，Val，Phe），2,3-二氨基丙酸作为分支单元，并在核心保留一个半胱氨酸残基。这些树状聚合物已被用作秋水仙碱的药物递送装置。秋水仙碱通过二硫键或硫醚键连接到半胱氨酸硫醇基团的树枝状聚合物上。在HeLa肿瘤细胞和未转化的小鼠胚胎成纤维细胞（MEF）中评估了糖肽树状聚合物结合物的生物学活性。发现通过干扰微管蛋白系统达到抑制细胞增殖所需的糖肽树状聚合物结合物的浓度比秋水仙碱浓度要高（IC50> 1 microM）。另一方面，糖肽树状大分子缀合物抑制HeLa细胞的增殖比MEF的增殖有效20到100倍。相比之下，非糖基化树状大分子和秋水仙碱本身对HeLa细胞的选择性是10倍或更低。

表征谱图