methyl 2,3-di-O-benzyl-6-chloro-6-deoxy-α-D-glucopyranoside | 67776-12-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-6-chloro-6-deoxy-α-D-glucopyranoside
• 英文别名: (2S,3S,4S,5R,6S)-2-(chloromethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 67776-12-9
• 化学式: C₂₁H₂₅ClO₅
• 分子量: 392.88
• InChiKey: HUDGNKSOTFCAQU-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6-chloro-6-deoxy-α-D-glucopyranoside 在 sodium hydroxide 、 tertiary amine 、 亚氨基二乙酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 2,3-di-O-benzyl-4-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel amino acid glycoside conjugates

  摘要：

  A new class of non-anomeric amino acid glycoconjugates can be prepared starting from either omega-amino- or omega-halodeoxyglucosides. Treatment of an ether-protected methyl 7-amino-6,7-dideoxy-alpha-D-glucoheptopyranoside with methyl aspartate isocyanate gave an urea-linked conjugate of methyl glucoheptopyranoside and aspartic acid. Nucleophilic displacement of the ether-protected methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside with potassium succinimide followed by imide ring opening and amidation of the succinic acid monoamide with dimethyl iminodiacetate led to a conjugate of methyl 6-amino-6-deoxy-alpha-D-glucopyranoside and iminodiacetate bridged by succinate. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00091-8
• 作为产物：
  描述：

  2,3-二-o-苄基-alpha-d-吡喃葡萄糖苷甲酯 在 六氯乙烷 、 potassium chloride 、 三苯基膦 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以95%的产率得到methyl 2,3-di-O-benzyl-6-chloro-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Halogenation of carbohydrates by triphenylphosphine complex reagents in highly concentrated solution under microwave activation or conventional heating

  摘要：

  Halogenation of carbohydrates with triphenylphosphine and carbon tetrachloride, hexachloroethane or 1,2-dibromotetrachloroethane was shown to be very efficient in highly concentrated solutions of nonpolar solvents such as toluene or 1,2-dichloroethane, with, in some cases, addition of potassium chloride, potassium bromide, and/or pyridine. The reactions were very fast under microwave irradiation (2 to 30 min) as well as by classical heating (2 to 45 min) at 80-120 degrees C. Most often, the yields were better under microwave irradiation and the reaction product distribution was sometimes different from that obtained with classical methods with, in all experiments, the amount of solvent strongly reduced. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00224-9

文献信息

• Halogenation of carbohydrates by triphenylphosphine complex reagents in highly concentrated solution under microwave activation or conventional heating
  作者：Corinne Limousin、Alain Olesker、Jeannine Cléophax、Alain Petit、André Loupy、Gabor Lukacs

  DOI：10.1016/s0008-6215(98)00224-9

  日期：1998.11

  Halogenation of carbohydrates with triphenylphosphine and carbon tetrachloride, hexachloroethane or 1,2-dibromotetrachloroethane was shown to be very efficient in highly concentrated solutions of nonpolar solvents such as toluene or 1,2-dichloroethane, with, in some cases, addition of potassium chloride, potassium bromide, and/or pyridine. The reactions were very fast under microwave irradiation (2 to 30 min) as well as by classical heating (2 to 45 min) at 80-120 degrees C. Most often, the yields were better under microwave irradiation and the reaction product distribution was sometimes different from that obtained with classical methods with, in all experiments, the amount of solvent strongly reduced. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of novel amino acid glycoside conjugates
  作者：Thorsten Heidelberg、Joachim Thiem

  DOI：10.1016/s0008-6215(97)00091-8

  日期：1997.6

  A new class of non-anomeric amino acid glycoconjugates can be prepared starting from either omega-amino- or omega-halodeoxyglucosides. Treatment of an ether-protected methyl 7-amino-6,7-dideoxy-alpha-D-glucoheptopyranoside with methyl aspartate isocyanate gave an urea-linked conjugate of methyl glucoheptopyranoside and aspartic acid. Nucleophilic displacement of the ether-protected methyl 6-chloro-6-deoxy-alpha-D-glucopyranoside with potassium succinimide followed by imide ring opening and amidation of the succinic acid monoamide with dimethyl iminodiacetate led to a conjugate of methyl 6-amino-6-deoxy-alpha-D-glucopyranoside and iminodiacetate bridged by succinate. (C) 1997 Elsevier Science Ltd.