α-D-2-O-acetyl-glucopyranose | 134677-29-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-2-O-acetyl-glucopyranose
• 英文别名: 2-O-acetyl α-D-glucose；I+/--D-Glucopyranose, 2-acetate；[(2S,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl] acetate
• CAS: 134677-29-5
• 化学式: C₈H₁₄O₇
• 分子量: 222.195
• InChiKey: ANUMJPWPBOXOQE-CBQIKETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  benzyl 4,6-O-benzylidene-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 二正丁基氧化锡 、 三乙胺 、 三氟乙酸 作用下， 生成 α-D-2-O-acetyl-glucopyranose
  参考文献：
  名称：

  On the analogy between forskolin and D-glucose

  摘要：

  2-O-Acetyl-D-glucose was synthesized in order to evaluate the influence of an acyl group on the binding with the glucose carrier protein (GluT); as its affinity neighbours that of glucose itself, the glucose forskolin analogy appears to be coincidental and several explanations are proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00270-x

文献信息

• <i>In situ</i>proton NMR study of acetyl and formyl group migration in mono-<i>O</i>-acyl D-glucose
  作者：Lothar Brecker、Marek Mahut、Alexandra Schwarz、Bernd Nidetzky

  DOI：10.1002/mrc.2395

  日期：2009.4

  Acetyl and formyl group migration, mutarotation, and hydrolysis of mono-O-acylated glucose are studied by in situ 1D and 2D (1)H NMR spectroscopy. Alpha-D-glucosyl-1-acetate and alpha-D-glucosyl-1-formate serve as sole starting materials. They are generated in situ by configuration retaining glucosyltransfer from alpha-D-glucosyl-1-phosphate to formate and acetate, which is catalyzed by the Glu-237

  通过原位1D和2D（1）H NMR光谱研究了单O酰化葡萄糖的乙酰基和甲酰基迁移，诱变和水解。α-D-葡萄糖基-1-乙酸酯和α-D-葡萄糖基-1-甲酸酯是唯一的起始原料。它们是通过保留从α-D-D-葡糖基-1-磷酸到甲酸和乙酸盐的葡糖基转移的构型而原位生成的，而这种转移是由肠膜肠隐球菌蔗糖磷酸化酶的Glu-237-> Gln突变体催化的。直接从反应混合物中鉴定，表征和定量临时累积的区域异构的单-O-酰基D-葡萄糖。转化的时程使人们了解了酰基迁移和诱变的pH依赖性以及各种区域异构体的稳定性。
• Selective Anomeric Acetylation of Unprotected Sugars with Acetic Anhydride in Water
  作者：Xin Qiu、Daniel Chong、Antony J. Fairbanks

  DOI：10.1021/acs.orglett.3c00584

  日期：2023.3.24

  Unprotected sugars are selectively acetylated simply by stirring in aqueous solution in the presence of acetic anhydride and a weak base such as sodium carbonate. The reaction is selective for acetylation of the anomeric hydroxyl group of mannose, 2-acetamido, and 2-deoxy sugars and can be performed on a large scale. Competitive intramolecular migration of the 1-O-acetate to the 2-hydroxyl group when

  在存在乙酸酐和弱碱（如碳酸钠）的情况下，只需在水溶液中搅拌，即可选择性地乙酰化未受保护的糖。该反应对甘露糖、2-乙酰氨基和 2-脱氧糖的异头羟基的乙酰化具有选择性，并且可以大规模进行。当这两个取代基为顺式时， 1- O-乙酸酯分子内竞争性迁移至 2-羟基会导致过度反应并形成产物混合物。
• CAPON, BRIAN;LEE, YIU-CHUNG, J. ORG. CHEM., 56,(1991) N4, C. 4428-4435
  作者：CAPON, BRIAN、LEE, YIU-CHUNG

  DOI：——

  日期：——
• PROTECTING AND LINKING GROUPS FOR ORGANIC SYNTHESIS
  申请人：Alchemia Pty. Ltd.

  公开号：EP1017683A1

  公开（公告）日：2000-07-12
• EP1017683A4
  申请人：——

  公开号：EP1017683A4

  公开（公告）日：2002-03-06