allyl 3-O-methyl-α-D-mannopyranoside | 187732-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-methyl-α-D-mannopyranoside
• 英文别名: (2R,3R,4S,5S,6S)-2-(hydroxymethyl)-4-methoxy-6-prop-2-enoxyoxane-3,5-diol
• CAS: 187732-04-3
• 化学式: C₁₀H₁₈O₆
• 分子量: 234.249
• InChiKey: UHTQSZWMOSRMPV-ZJDVBMNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 3-O-methyl-α-D-mannopyranoside 在 盐酸 、 sodium hydride 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 9.25h， 生成 allyl 2,6-dibenzyl-3-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a hexasaccharide acceptor corresponding to the reducing terminus of mycobacterial 3-O-methylmannose polysaccharide (MMP)

  摘要：

  The title compound methyl O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)-[(1 --> 4)- O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)](4)-(1 --> 4)-2,6-di-O-benzyl-3-O-methyl-alpha-D- mannopyranoside (2) was synthesized in a blockwise manner, employing trichloroacetimidate (11) and (20) as glycosyl donors. The strategy relies on the single-step preparation of the 3-O-methyl ethers (4) and (12) as starting materials. Since all intermediates contain one or more OCH3 groups, they are easily identified by NMR spectroscopy using the methyl proton signals, Compound 2 corresponds to the reducing terminal hexasaccharide of mycobacterial 3-O-methylmannose polysaccharide (MMP). MMP has the unusual property of stimulating the fatty acid synthetase multienzyme complex. Compound 2 can serve as a suitable glycosyl acceptor for the synthesis of extended fragments of MMP. (C) 1996 Elsevier Science-Ltd.

  DOI：

  10.1016/s0008-6215(96)00239-x
• 作为产物：
  描述：

  烯丙基alpha-D-吡喃甘露糖苷 、 碘甲烷 在 二正丁基氧化锡 作用下， 生成 allyl 3-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  A single-step synthesis of methyl 3-O-methyl-α-d-manno-, -α-d-galacto-, -α-l-rhamno-, and -α-l-fuco-pyranoside

  摘要：

  DOI：

  10.1016/0008-6215(94)80030-8

文献信息

• A single-step synthesis of methyl 3-O-methyl-α-d-manno-, -α-d-galacto-, -α-l-rhamno-, and -α-l-fuco-pyranoside
  作者：Wensheng Liao、Yu Liu、Depei Lu

  DOI：10.1016/0008-6215(94)80030-8

  日期：1994.7
• Synthesis of a hexasaccharide acceptor corresponding to the reducing terminus of mycobacterial 3-O-methylmannose polysaccharide (MMP)
  作者：Wensheng Liao、Depei Lu

  DOI：10.1016/s0008-6215(96)00239-x

  日期：1996.12

  The title compound methyl O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)-[(1 --> 4)- O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)](4)-(1 --> 4)-2,6-di-O-benzyl-3-O-methyl-alpha-D- mannopyranoside (2) was synthesized in a blockwise manner, employing trichloroacetimidate (11) and (20) as glycosyl donors. The strategy relies on the single-step preparation of the 3-O-methyl ethers (4) and (12) as starting materials. Since all intermediates contain one or more OCH3 groups, they are easily identified by NMR spectroscopy using the methyl proton signals, Compound 2 corresponds to the reducing terminal hexasaccharide of mycobacterial 3-O-methylmannose polysaccharide (MMP). MMP has the unusual property of stimulating the fatty acid synthetase multienzyme complex. Compound 2 can serve as a suitable glycosyl acceptor for the synthesis of extended fragments of MMP. (C) 1996 Elsevier Science-Ltd.