3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride | 5605-82-3

• 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
• 英文名称: 3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride
• 英文别名: [(2R,3R,4R,5R,6R)-3,4-diacetyloxy-6-chloro-5-hydroxyoxan-2-yl]methyl acetate
• CAS: 5605-82-3
• 化学式: C₁₂H₁₇ClO₈
• 分子量: 324.715
• InChiKey: WCYKMRJTYLWEET-OOCWMUITSA-N

物化性质

• 熔点：
  93-94 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  417.1±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride 在 吡啶 、 磷酸酐 、 calcium sulfate 、 sodium tetrahydroborate 、 sodium methylate 、 silver carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 21.5h， 生成 4-硝基苯基-BETA-D-吡喃甘露糖苷
  参考文献：
  名称：

  Synthesis of 4-nitrophenyl 2,3,6-tri-O-acetyl-4-deoxy-β-d-lyxo-hexopyranoside and a new synthesis of 4-nitrophenyl β-d-mannopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(83)84067-1
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-β-D-glucopyranosyl chloride 在 丙酮 作用下， 生成 3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride
  参考文献：
  名称：

  THE ALPHA AND BETA 1,3,4,6-TETRAACETYL-D-GLUCOPYRANOSES AND THEIR CHLOROACETYL DERIVATIVES

  摘要：

  3,4,6-三乙酰基-β-D-葡萄糖吡喃基氯化物与醋酸银在冰醋酸中反应得到1,3,4,6-四乙酰基-α-D-葡萄糖吡喃糖，熔点97-98°C，[α]D +145°（氯仿）。3,4,6-三乙酰基-α-D-葡萄糖吡喃基氯化物，熔点93-94°C，[α]D +185°（氯仿），由β异构体在丙酮中异构化制备，与醋酸银在冰醋酸中反应得到1,3,4,6-四乙酰基-β-D-葡萄糖吡喃糖，熔点137-138°C，[α]D +26°（氯仿）。这些葡萄糖四乙酰基的结构是通过氯乙酰衍生物的相互转化确定的。

  DOI：

  10.1139/v53-136

文献信息

• THE SOLVOLYSIS OF THE <i>ALPHA</i>- AND <i>BETA</i>-<scp>3,4,6</scp>-TRI-<i>O</i>-ACETYL-<scp>D</scp>-GLUCOPYRANOSYL CHLORIDES
  作者：R. U. Lemieux、G. Huber

  DOI：10.1139/v55-016

  日期：1955.1.1

  3,4,6-Tri-O-acetyl-β-D-glucopyranosyl chloride was found to undergo solvolysis in acetic acid to form 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose as the main reaction product. The much less reactive anomeric α-chloride also appeared to undergo solvolysis with extensive inversion of the anomeric center. It is submitted that the tendencies for inversion obtained in these ionic reactions are due to the conformations imposed on the intermediate ions through distribution of the positive charge to the ring oxygen and the consequent introduction of double-bond character to the carbon-1 to ring-oxygen bond.

  3,4,6-三-O-乙酰基-β-D-葡萄糖吡喃糖氯化物在醋酸中发生溶剂解作用，形成1,3,4,6-四-O-乙酰基-α-D-葡萄糖吡喃糖作为主要反应产物。反应活性较低的顺式α-氯化物也似乎发生了溶剂解作用，并且在异构中心进行了广泛的反转。认为这些离子反应中获得的反转趋势是由于通过将正电荷分布到环氧原子上并引入双键特性到碳-1到环氧原子键上所施加的中间离子的构象。
• STABLE VITAMIN B6 DERIVATIVE
  申请人：Daiichi Fine Chemical Co., Ltd.

  公开号：EP1679316A1

  公开（公告）日：2006-07-12

  A compound represented by the following general formula (I) or a salt thereof: wherein R1 represents a glycosyl group, a phosphate group, or a cyclic phosphate group bound to R2; R2 represents -CH2OH, -CHO, -CH2NH2, -CH2-amino acid residue, or -CH2-OPO2H; and R3 represents hydrogen atom, or -PO3H2, and a composition for cosmetics, medicaments, foodstuffs, and/or feeds containing the aforementioned compound or a salt thereof.

  由以下通式 (I) 代表的化合物或其盐： 其中 R1 代表糖基、磷酸基或与 R2 结合的环磷酸基；R2 代表- OH、-CHO、- NH2、-CH2-氨基酸残基或- -OPO2H；R3 代表氢原子或-PO3H2，以及含有上述化合物或其盐的用于化妆品、药物、食品和/或饲料的组合物。
• Csueroes et al., Acta Chimica Academiae Scientiarum Hungaricae, 1959, vol. 21, p. 169,176
  作者：Csueroes et al.

  DOI：——

  日期：——
• Diphenylmethylation of carbohydrate hydroxyl groups by the reaction with diazo(diphenyl)methane
  作者：Graham Jackson、Haydn F. Jones、Sigthor Petursson、John M. Webber

  DOI：10.1016/s0008-6215(00)88058-1

  日期：1982.4
• Efficient synthesis of ω-mercaptoalkyl 1,2-trans-glycosides from sugar peracetates
  作者：Teiichi Murakami、Reiko Hirono、Yukari Sato、Kiyotaka Furusawa

  DOI：10.1016/j.carres.2007.02.024

  日期：2007.6

  Lewis acid-promoted reactions of peracetylated sugars (glucose, galactose, maltose, lactose) with omega-bromo-1-alkanols (C-8, C-12) were investigated. ZnCl2, was found to promote the 1,2-trans-glycosylation of the alcohols in toluene at about 60 degrees C in a stereocontrolled manner with better yields than commonly employed promoters such as SnCl4. The omega-bromoalkyl acetylated glycosides were readily converted to omega-mercaptoalkyl glycosides, which are useful for the preparation of glycoclusters. (c) 2007 Elsevier Ltd. All rights reserved.