methyl 2-deoxy-α,β-glycoside | 198011-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-deoxy-α,β-glycoside
• 英文别名: (2R,3R,4R)-6-methoxy-2-methyloxane-3,4-diol
• CAS: 198011-32-4
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: QNKOVWCOVLYPKR-FYBJJZIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-α,β-glycoside 在 吡啶 、 盐酸 、 三氟甲磺酸酐 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Two syntheses of 246-Trideoxy-4-methylthio-D-ribo-pyranose

  摘要：

  Two syntheses of 2,4,6-trideoxy-4-methylthio-D-ribo-pyranose, a component of the oligosaccharide of esperamicins are described: an asymmetric synthesis starting from the propargylic alcohol dimer and the stereocontrolled transformation of D-fucose.

  DOI：

  10.1016/0040-4039(93)88072-q
• 作为产物：
  描述：

  甲醇 、 6-deoxy-D-glucal 在 camphor-10-sulfonic acid 作用下， 以90%的产率得到methyl 2-deoxy-α,β-glycoside
  参考文献：
  名称：

  Two syntheses of 246-Trideoxy-4-methylthio-D-ribo-pyranose

  摘要：

  Two syntheses of 2,4,6-trideoxy-4-methylthio-D-ribo-pyranose, a component of the oligosaccharide of esperamicins are described: an asymmetric synthesis starting from the propargylic alcohol dimer and the stereocontrolled transformation of D-fucose.

  DOI：

  10.1016/0040-4039(93)88072-q

文献信息

• Synthesis of 2,6-dideoxy-4-S-methyl-4-thio-d-ribo-hexopyranose, a component of the esperamicin oligosaccharide
  作者：François-Yves Dupradeau、Jacques Prandi、Jean-Marie Beau

  DOI：10.1016/0040-4020(95)00059-h

  日期：1995.3

  Two synthetic approaches to 2,6-dideoxy-4-S-methyl-4-thio-D-ribo pyranose, a component of the oligosaccharide of esperamicins are described. An asymmetric synthesis, starting from the propargylic alcohol dimer, relies on the Sharpless asymmetric epoxidation and the regioselective opening of epoxy alcohols. The other synthesis is based on stereocontrolled transformations of a readily available sugar precursor, D-galactose.
• Environmentally benign aryl C-glycosidations of unprotected sugars using montmorillonite K-10 as a solid acid
  作者：Kazunobu Toshima、Yasunobu Ushiki、Goh Matsuo、Shuichi Matsumura

  DOI：10.1016/s0040-4039(97)01724-3

  日期：1997.10

  Highly practical aryl C-glycosidations of unprotected 1-OMe and 1-OH sugars with phenol and naphthol derivatives were effectively realized using montmorillonite K-10 as an environmentally compatible solid acid in CHCl3 or H2O. (C) 1997 Elsevier Science Ltd.