methyl 2,3,6-tri-O-benzyl-5-C-methoxy-β-D-glucopyranoside | 192372-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-5-C-methoxy-β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2,6-dimethoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 192372-91-1
• 化学式: C₂₉H₃₄O₇
• 分子量: 494.585
• InChiKey: PDHJJHZNLMBUMO-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-5-C-methoxy-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl 5-C-methoxy-β-D-glucopyranoside
  参考文献：
  名称：

  A new route to d-xylo-hexos-5-ulose and some of its selectively protected derivatives from d-galactose

  摘要：

  A new approach to D-xylo-hexos-5-ulose, a useful synthetic intermediate, is described, starting from methyl beta-D-galactopyranoside and involving as the key step an epoxidation/methanolysis of 3-O-protected methyl 2,6-di-O-benzyl-4-deoxy-alpha-L-threo-hex-4-enopyranosides, to produce bis-glycosides of the parent dicarbonylic sugar, which can be obtained free or selectively protected through hydrogenolytic and/or hydrolytic procedures. The diastereo- and regioselectivity of the epoxidation and solvolysis steps are investigated and tentatively interpreted, and new products characterized by NMR techniques, (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00536-x
• 作为产物：
  描述：

  甲醇 、 methyl 2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside 在 间氯过氧苯甲酸 作用下， 反应 24.0h， 以19%的产率得到methyl 2,3,6-tri-O-benzyl-5-C-methoxy-β-D-glucopyranoside
  参考文献：
  名称：

  A new route to d-xylo-hexos-5-ulose and some of its selectively protected derivatives from d-galactose

  摘要：

  A new approach to D-xylo-hexos-5-ulose, a useful synthetic intermediate, is described, starting from methyl beta-D-galactopyranoside and involving as the key step an epoxidation/methanolysis of 3-O-protected methyl 2,6-di-O-benzyl-4-deoxy-alpha-L-threo-hex-4-enopyranosides, to produce bis-glycosides of the parent dicarbonylic sugar, which can be obtained free or selectively protected through hydrogenolytic and/or hydrolytic procedures. The diastereo- and regioselectivity of the epoxidation and solvolysis steps are investigated and tentatively interpreted, and new products characterized by NMR techniques, (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00536-x

文献信息

• A new route to d-xylo-hexos-5-ulose and some of its selectively protected derivatives from d-galactose
  作者：Pier Lugi Barili、Giancarlo Berti、Giorgio Catelani、Felicia D'Andrea、Francesco De Rensis

  DOI：10.1016/s0040-4020(97)00536-x

  日期：1997.6

  A new approach to D-xylo-hexos-5-ulose, a useful synthetic intermediate, is described, starting from methyl beta-D-galactopyranoside and involving as the key step an epoxidation/methanolysis of 3-O-protected methyl 2,6-di-O-benzyl-4-deoxy-alpha-L-threo-hex-4-enopyranosides, to produce bis-glycosides of the parent dicarbonylic sugar, which can be obtained free or selectively protected through hydrogenolytic and/or hydrolytic procedures. The diastereo- and regioselectivity of the epoxidation and solvolysis steps are investigated and tentatively interpreted, and new products characterized by NMR techniques, (C) 1997 Elsevier Science Ltd.