methyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranoside | 6087-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranoside
• 英文别名: methyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-lyxo-hexopyranoside；methyl 3,4,6-tri-O-acetyl-2-deoxy-D-galactopyranoside；[(2R,3R,4R,6R)-3,4-diacetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 6087-43-0
• 化学式: C₁₃H₂₀O₈
• 分子量: 304.297
• InChiKey: JTQYAWBAXLZBQR-FDYHWXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 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

• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三甲基溴硅烷 、 氢溴酸 、 溶剂黄146 、 三苯基氧化膦 作用下， 以 二氯甲烷 为溶剂， -15.0~20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 methyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranoside 、 methyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactoside
  参考文献：
  名称：

  TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

  摘要：

  甘露糖醛酸盐的硫加成反应可以在无溶剂条件下高效地通过等物量的溴化三甲基硅(TMSBr)催化产生良好至优异收率的S-2-脱氧糖苷。此外，加入三苯基膦氧化物作为添加剂，TMSBr介导的甘露糖醛酸盐与多种醇类的直接糖基化反应具有高度α-选择性。

  DOI：

  10.3762/bjoc.12.164

文献信息

• Syntheses of β-2-deoxy-D-glycosides assisted by glycosidases
  作者：Jean-Michel Petit、Françoise Paquet、Jean-Marie Beau

  DOI：10.1016/0040-4039(91)80769-3

  日期：1991.10

  Enzyme-catalyzed preparation of β-2-deoxy-D-glucosides and galactosides including disaccharides has been achieved using the corresponding glycals as substrates.

  使用相应的糖基作为底物，已经实现了酶催化的β-2-脱氧-D-葡萄糖苷和半乳糖苷（包括二糖）的制备。
• Ferrier Rearrangement and 2-Deoxy Sugar Synthesis from d-Glycals Mediated by Layered α-Zirconium Sulfophenylphosphonate-Methanphosphonate as Heterogeneous Catalyst
  作者：Ornelio Rosati、Massimo Curini、Federica Messina、Maria Carla Marcotullio、Giancarlo Cravotto

  DOI：10.1007/s10562-012-0932-z

  日期：2013.2

  conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate-methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields.Graphical Abstract

  层状 α-磺基苯基膦酸锆 - 甲膦酸是一种固体酸催化剂，可在温和的反应条件下，在短时间内和良好的产率催化 d-乙二醇和醇类亲核试剂的费里尔重排。值得注意的是，α-磺基苯基膦酸锆-甲膦酸锆和溴化锂的组合改变了该过程的区域选择性，以良好的收率提供了 2-脱氧糖。
• The use of tri-O-acetyl-d-glucal and -d-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides
  作者：Beata Liberek、Aleksandra Dąbrowska、Ryszard Frankowski、Marlena Matuszewska、Zygfryd Smiatacz

  DOI：10.1016/s0008-6215(02)00288-4

  日期：2002.11

  Addition of hydrazoic acid to alpha, beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the H-1 and C-13 NMR, IR and polarimetric data. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of 2-deoxy sugars from glycals
  作者：Subramaniam Sabesan、Susana Neira

  DOI：10.1021/jo00018a054

  日期：1991.8
• US5128463A
  申请人：——

  公开号：US5128463A

  公开（公告）日：1992-07-07