methyl 2,3-di-O-benzyl-6-bromo-6-deoxy-α-D-galactopyranoside | 129077-17-4

• 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-bromo-6-deoxy-α-D-galactopyranoside
• 英文别名: (2S,3R,4S,5R,6S)-2-(bromomethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 129077-17-4
• 化学式: C₂₁H₂₅BrO₅
• 分子量: 437.331
• InChiKey: JDPQCCRYEHMFKB-IFLJBQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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-bromo-6-deoxy-α-D-galactopyranoside 在 sodium cyanoborohydride 、 三苯基膦 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-2-vinyl-pyrrolidine
  参考文献：
  名称：

  一种简短的通用方法，利用还原消除-还原胺化作为关键步骤来制备多羟基化吡咯烷

  摘要：

  由甲基4，6-亚苄基葡萄糖和吡喃半乳糖苷开始的高效异构体α-乙烯基吡咯烷酮的合成容易获得羟基化的吡咯烷酮。

  DOI：

  10.1016/0040-4039(90)87010-w
• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 在 吡啶 、 四溴化碳 、 硫酸 、 camphor-10-sulfonic acid 、 sodium hydride 、 三苯基膦 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 methyl 2,3-di-O-benzyl-6-bromo-6-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  PdCl2/CuCl2-catalysed chlorocyclisation of sugar-derived aminoalkenitols in the synthesis of new iminohexitols

  摘要：

  The total synthesis of two novel L-ido and L-altro configured 6-chloro-1,5,6-trideoxyiminohexitols featuring a highly diastereoselective Pd(II)/CuCl2-catalysed chlorocyclisation of sugar-derived aminoalkenitols has been accomplished. The requisite substrates were, in turn, prepared from chiral pool materials starting from the cheap and commercially available methyl-alpha-D-gluco- and methyl-a-D-galactopyranoside. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.078

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.
• BERNOTAS, RONALD C., TETRAHEDRON LETT., 31,(1990) N, C. 469-472
  作者：BERNOTAS, RONALD C.

  DOI：——

  日期：——
• PdCl2/CuCl2-catalysed chlorocyclisation of sugar-derived aminoalkenitols in the synthesis of new iminohexitols
  作者：Peter Szolcsányi、Tibor Gracza

  DOI：10.1016/j.tet.2006.06.078

  日期：2006.9

  The total synthesis of two novel L-ido and L-altro configured 6-chloro-1,5,6-trideoxyiminohexitols featuring a highly diastereoselective Pd(II)/CuCl2-catalysed chlorocyclisation of sugar-derived aminoalkenitols has been accomplished. The requisite substrates were, in turn, prepared from chiral pool materials starting from the cheap and commercially available methyl-alpha-D-gluco- and methyl-a-D-galactopyranoside. (c) 2006 Elsevier Ltd. All rights reserved.
• A short, versatile approach to polyhydroxylated pyrrolidines utilizing a reductive elimination-reductive amination as a key step
  作者：Ronald C Bernotas

  DOI：10.1016/0040-4039(90)87010-w

  日期：1990.1

  An efficient synthesis of epimeric alpha-vinyl pyrrolidines starting from methyl 4,6--benzylidene gluco- and galactopyranosides gave ready access to hydroxylated pyrrolidines.

  由甲基4，6-亚苄基葡萄糖和吡喃半乳糖苷开始的高效异构体α-乙烯基吡咯烷酮的合成容易获得羟基化的吡咯烷酮。