methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside | 7404-32-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside
• 英文别名: methyl 2,3,4-tri-O-acetyl-6-deoxy-6-bromo-α-D-glucopyranoside；methyl-2,3,4-tri-O-acetyl-6-deoxy-6-bromo-a-D-glucopyranoside；methyl-[tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside；Methyl-[tri-O-acetyl-6-brom-6-desoxy-α-D-glucopyranosid；Methyl-2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranosid；Methyl-6-brom-6-desoxy-2,3,4-tri-O-acetyl-α-D-glucopyranosid；a-D-Glucopyranoside,methyl6-bromo-6-deoxy-,2,3,4-triacetate；[(2S,3S,4S,5R,6S)-4,5-diacetyloxy-2-(bromomethyl)-6-methoxyoxan-3-yl] acetate
• CAS: 7404-32-2
• 化学式: C₁₃H₁₉BrO₈
• 分子量: 383.193
• InChiKey: JEEGQLMJZGMZSR-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside 在 甲醇 、 氨 作用下， 生成 methyl 6-bromo-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Helferich et al., Chemische Berichte, 1926, vol. 59, p. 79,83

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基-6-叠氮-6-脱氧-2,3,4-三乙酰氧基-alpha-D-吡喃葡萄糖苷 在 nitrosyl hexafluorophosphate 、 四乙基溴化铵 作用下， 生成 methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Jacobsen, Steffen, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 2, p. 157 - 164

  摘要：

  DOI：

文献信息

• A Novel Protocol for the Regioselective Bromination of Primary Alcohols in Unprotected Carbohydrates or Glycosides
  作者：Weihua Xue、Lifen Zhang

  DOI：10.1002/cjoc.201200211

  日期：2012.7

  The regioselective and efficient bromination of primary hydroxyl groups in unprotected carbohydrates or glycosides is successfully achieved by using (chloro‐phenylthio‐methylene)dimethylammoniumchloride (CPMA) in the presence of tetrabutylammonium bromide (TBAB) in dry DMF.

  在干燥的DMF中，在四丁基溴化铵（TBAB）存在下，使用（氯-苯硫基-亚甲基）二甲基氯化铵（CPMA）成功地实现了未保护的碳水化合物或糖苷中伯羟基的区域选择性和有效溴化。
• Synthesis of Thioglycosides by Tetrathiomolybdate-Mediated Michael Additions of Masked Thiolates
  作者：Perali�Ramu Sridhar、Kandikere�Ramaiah Prabhu、Srinivasan Chandrasekaran

  DOI：10.1002/ejoc.200400360

  日期：2004.12

  for the synthesis of thioglycosides in excellent yields under neutral conditions through the use of benzyltriethylammonium tetrathiomolybdate $[(BnNEt_3)}_2MoS_4; 1]$ as a sulfur-transfer reagent has been developed. The reagent 1 reacts with sugar halides to give sugar disulfides, which then undergo reductive cleavage in situ to provide the corresponding thiolates, followed by Michael addition to give

  通过使用四硫代钼酸苄基三乙基铵 $[(BnNEt_3)}_2MoS_4; 在中性条件下以优异的收率合成硫糖苷的有效一锅法；1]$ 作为硫转移试剂已被开发出来。试剂 1 与糖卤化物反应生成糖二硫化物，然后进行原位还原裂解以提供相应的硫醇盐，然后通过迈克尔加成得到相应的硫代糖苷。此外，通过使用四硫代钼酸铵 $[(NH_4)}_2 MoS_4; 2]$。这种方法的应用已扩展到通过分子间和分子内反应合成具有优异非对映选择性的各种硫糖类似物。
• Selective Synthesis Under Microwave Irradiation of Carbohydrate Derivatives Containing Unsaturated Systems
  作者：Marta M. Andrade、Maria Teresa Barros、Paula Rodrigues

  DOI：10.1002/ejoc.200700154

  日期：2007.8

  The selective synthesis of sugars containing vinyl ester- and vinyl ether-type side chains was developed by means of esterification and Wittig olefination procedures. The studies were focused on the anomeric position of D-xylose and on the primary carbon positions of D-glucose and sucrose. Microwave heating was used in both cases, and the results obtained show the usefulness of microwave irradiation

  含有乙烯基酯和乙烯基醚型侧链的糖的选择性合成是通过酯化和 Wittig 烯化程序开发的。研究集中在 D-木糖的异头位置以及 D-葡萄糖和蔗糖的主要碳位置。在这两种情况下都使用了微波加热，所获得的结果表明微波辐射对于开发碳水化合物化学清洁技术的有用性。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite
  作者：Cheerladinne Venkateswarlu、Vibha Gautam、Srinivasan Chandrasekaran

  DOI：10.1016/j.carres.2014.07.011

  日期：2014.9

  A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-D-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.
• Synthesis of mixed glycosyl disulfides/selenenylsulfides using benzyltriethylammonium tetrathiomolybdate as a sulfur transfer reagent
  作者：Cheerladinne Venkateswarlu、Vibha Gautam、Srinivasan Chandrasekaran

  DOI：10.1016/j.carres.2014.09.005

  日期：2015.1

  An easy and mild method has been developed for the synthesis of mixed glycosyl disulfides/selenenylsulfides from glycosyl halides and diaryl/dialkyl dichalcogenides in the presence of benzyltriethylammonium tetrathiomolybdate [(BnEt3N)(2)MoS4]. The salient feature of this method is the sulfur transfer from [BnEt3N](2)MoS4 to form glycosyl disulfides which with excess tetrathiomolybdate further undergo exchange reaction with other dichalcogenides in a one-pot operation. (C) 2014 Elsevier Ltd. All rights reserved.