methyl 2,3,4-tri-O-mesyl-α-D-glucopyranoside | 76947-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-mesyl-α-D-glucopyranoside
• 英文别名: methanesulfonic acid 2-hydroxymethyl-4,5-bis(methanesulfonyloxy)-6-methoxytetrahydropyran-3-yl ester；[(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-methoxy-4,5-bis(methylsulfonyloxy)oxan-3-yl] methanesulfonate
• CAS: 76947-07-4
• 化学式: C₁₀H₂₀O₁₂S₃
• 分子量: 428.46
• InChiKey: ZEYGMBORZWDUCO-SPFKKGSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.62
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  168.8
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  methyl 2,3,4,6-tetra-O-mesyl-α-D-glucopyranoside 在 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 methyl 2,3,4-tri-O-mesyl-α-D-glucopyranoside
  参考文献：
  名称：

  Products from the base treatment of the tri-O- and tetra-O-methanesulfonyl esters of methyl .alpha.-D-glucopyranoside

  摘要：

  DOI：

  10.1021/jo00325a005

文献信息

• A Facile, Catalytic, and Environmentally Benign Method for Selective Deprotection of <i>tert</i>-Butyldimethylsilyl Ether Mediated by Phosphomolybdic Acid Supported on Silica Gel
  作者：G. D. Kishore Kumar、Sundarababu Baskaran

  DOI：10.1021/jo0502697

  日期：2005.5.1

  An environmentally benign PMA supported on SiO2 is found to be an efficient catalyst for the chemoselective deprotection of TBDMS ethers under very mild conditions. Various labile functional groups such as isopropylidene acetal, OTBDPS, OTHP, Oallyl, OBn, alkene, alkyne, OAc, OBz, N-Boc, N-Cbz, N-Fmoc, mesylate, and azide are found to be stable under the reaction conditions. This "truly catalytic" heterogeneous reaction does not require aqueous workup, and the supported catalyst and the solvent can be readily recovered and recycled.