methyl 2,3-di-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside | 129077-21-0

• 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-glucopyranoside
• 英文别名: (2S,3S,4S,5R,6S)-2-(bromomethyl)-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 129077-21-0
• 化学式: C₂₁H₂₅BrO₅
• 分子量: 437.331
• InChiKey: JDPQCCRYEHMFKB-ADAARDCZSA-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-glucopyranoside 在 palladium on activated charcoal 四氧化锇 、 氢气 、 sodium cyanoborohydride 、 N-甲基吗啉氧化物 、 三苯基膦 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 为溶剂， 生成 1,4-dideoxy-1,4-imino-D-galacitol hydrochloride
  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：

  甲基-4,6-O-亚苄基-Α-D-吡喃葡糖苷 在 四溴化碳 、 硫酸 、 sodium hydride 、 三苯基膦 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2,3-di-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside
  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

文献信息

• Total synthesis of new C-6 homologues of 1-deoxynojirimycin and 1-deoxy-l-idonojirimycin
  作者：Peter Szolcsányi、Tibor Gracza、Marian Koman、Naïa Prónayová、Tibor Liptaj

  DOI：10.1039/a908449e

  日期：——

  Novel piperidine lactones 1 and 2, which represent direct precursors to the new C-6 homologues of 1-deoxynojirimycin (3) and 1-deoxy-L-idonojirimycin 4, were prepared by key PdII-catalysed aminocarbonylation of protected aminoalkene 10.

  新型哌啶内酯 1 和 2 是 1-脱氧野尻霉素 (3) 和 1-脱氧-L-idonojirimycin 4 的新 C-6 同系物的直接前体，是通过关键 PdII 催化的受保护氨基烯烃 10 的氨基羰基化制备的。
• Structure and Reactions of Glycopyranoside Derived Dialdehydes
  作者：Thorsten Heidelberg、Joachim Thiem

  DOI：10.1002/prac.19983400305

  日期：——

  Several 4- protected D-glucopyranosides were synthesized and cleaved by sodium metaperiodate. Depending on the protection pattern the resulting dialdehydes showed different types of structures. Predominantly dioxane structures of the hemiacetal or hemialdal type were obtained with preferred trans orientation of the exo oxygen groups at C-1 and C-2. The dialdehyde derived from methyl 4-O-methyl-alpha-D-glucopyranoside was treated with various C-nucleophiles. A higher reactivity of the aldehyde function at the former C-3 in comparison to C-2 and a special stability of dioxane type structures for glycol cleavage dialdehydes derived was observed.
• 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.
• Pd(II)-catalysed aminocarbonylation as a key step in the total synthesis of C-6 homologues of 1-deoxynojirimycin and 1-deoxy-l-idonojirimycin
  作者：Peter Szolcsányi、Tibor Gracza、Marian Koman、N Prónayová、Tibor Liptaj

  DOI：10.1016/s0957-4166(00)00226-3

  日期：2000.6

  The first successful Pd(II)-catalysed aminocarbonylation of the highly substituted benzylaminoalkene 5 allo ws the direct preparation of fused piperidine lactones 3 and 4, which are subsequently converted to the novel C-6 homologue of 1-deoxynojirimycin 1 and 1-deoxy-L-idonojirimycin 2. The study of the influence of various catalytic conditions on the diastereoselectivity and product distribution of the key amino-carbonylation is presented. (C) 2000 Elsevier Science Ltd. All rights reserved.