methyl 6-O-benzyl-β-D-galactopyranoside | 67393-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-benzyl-β-D-galactopyranoside
• 英文别名: Methyl 6-O-benzyl-β-D-galaktopyranosid
• CAS: 67393-10-6
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: UUEYXODSFDWAMJ-MBJXGIAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  88.38
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 6-O-benzyl-β-D-galactopyranoside 在 palladium on activated charcoal 、 铂 3 A molecular sieve 、 硫酸 、 氧气 、 碳酸氢钠 、 溶剂黄146 作用下， 反应 10.0h， 生成 methyl 3,4-O-<1-(methoxycarbonyl)ethylidene>-β-D-galactopyranoside
  参考文献：
  名称：

  甲基β-d-吡喃半乳糖苷的O-（1-羧乙叉）衍生物的13C-NMR光谱性质：多糖中丙酮酸缩醛结构的测定模型

  摘要：

  摘要记录了与半乳糖吡喃糖和褐藻糖衍生物连接的O-（1-羧乙叉基）化合物的CN.mr光谱。这些化合物可用作确定多糖中丙酮酸缩醛取代基的位置和构型的辅助剂。非质子化缩醛碳的化学位移取决于缩醛环是5元（δc 107-109.5）还是6元（δc 100.5-102.4）。3,4-（1-羧乙叉基）乙缩醛的C-3信号很典型，在〜δc 81处，对于甲基β-d-吡喃半乳糖苷衍生物的钡盐而言。确切值取决于配置，无论是6（δc 81.1）还是5（δc 80.4）。质子-核磁共振谱的CH 3信号在诊断上也有用，分别位于δ1.97和2.07。（上述移位值是pH依赖性的）。来自蜗牛的丙酮酸半乳聚糖，Pomacea lineata，显示含有一些残基，这些残基可以被分配一个在乙缩醛取代和乙缩醛构型对应于结构6的结构。化合物6（钡盐）是令人感兴趣的，因为当通过常规方法获得时，其13 Cn.mr光谱缺乏非质子化的羰基和乙缩醛碳共振。尽管这主要是由于T

  DOI：

  10.1016/s0008-6215(00)81021-6
• 作为产物：
  描述：

  methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 在 溶剂黄146 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 6-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  The structure of 5-membered acetal groups of pyruvic acid in the d-galactan of the snail Pomacea lineata

  摘要：

  DOI：

  10.1016/s0008-6215(00)85996-0

文献信息

• Substituent effects on the regioselectivity of enzymatic acylation of 6-O-alkylglycopyranosides using Pseudomonas cepacia lipase
  作者：David A. MacManus、Evgeny N. Vulfson

  DOI：10.1016/0008-6215(95)00292-8

  日期：1995.12

  Abstract The regioselectivity of acylation of a range of 6- O -protected glycosides using Pseudomonas cepacia lipase in vinyl acetate was investigated. In general, α-glycosides were acylated at the O-2 position and β-glycosides were acylated at the O-3 position. The effects of varying the size/hydrophobicity of the O-6 and anomeric substituents on the regioselectivity of the reaction are discussed

  摘要研究了假单胞菌洋葱脂肪酶在乙酸乙烯酯中酰化一系列6-O-保护的糖苷的区域选择性。通常，α-糖苷在O-2位被酰化，而β-糖苷在O-3位被酰化。根据底物在酶活性位点上的结合，讨论了改变O-6和端基异构体取代基的大小/疏水性对反应区域选择性的影响。
• An efficient, unambiguous synthesis of methyl 3-O-β-d-galactopyranosyl-β-d-galactopyranoside. Further studies on the specificity of antigalactopyranan monoclonal antibodies
  作者：Pavol Kováč、Cornelis P.J. Glaudemans、Richard B. Taylor

  DOI：10.1016/s0008-6215(00)90746-8

  日期：1985.10
• Selective benzylation of some d-galactopyranosides
  作者：Harold M. Flowers

  DOI：10.1016/s0008-6215(00)81052-6

  日期：——
• Halide promoted organotin-mediated carbohydrate benzylation: mechanism and application
  作者：Yixuan Zhou、Jinyang Li、Yingjie Zhan、Zhichao Pei、Hai Dong

  DOI：10.1016/j.tet.2013.02.024

  日期：2013.4

  In the present study, the mechanistic origin of the promoted organotin-mediated carbohydrate benzylation by halides was explored by the comparison of the activation ability of halides on benzylation of methyl beta-D-galactoside. It was demonstrated that the improvement of benzylation in terms of speed, yield and general convenience in the presence of halides was due to the formation of an activated oxide species by the coordination of halide anions to the tetracoordinate tin atoms. The halide, being able to form a stronger bond with tin, showed stronger activation ability. The catalytic amount of bromide should be preferentially chosen as an activation additive in the reaction with consideration of economy, convenience and moderate activation ability. The results were further applied to mono- and multibenzylation of additional carbohydrate structures. A range of prototype carbohydrate structures were efficiently prepared with the guidance of the principle. In light of the previous studies and the present experimental results, the general rules for organotin-mediated benzylation of carbohydrates have been summarized. (C) 2013 Elsevier Ltd. All rights reserved.
• An approach to regioselective alkylation of alkyl β-d-galactopyranosides through (trialkylstannyl)ation
  作者：Tomoya Ogawa、Tomoo Nukada、Masanao Matsui

  DOI：10.1016/s0008-6215(00)81006-x

  日期：1982.3