methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside | 216577-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside
• 英文别名: (2R,3R,4R,5R,6R)-2,6-dimethoxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxane-3,4-diol
• CAS: 216577-78-5
• 化学式: C₂₂H₂₈O₇
• 分子量: 404.46
• InChiKey: AFXTUILJCXPQFS-ZSYZGHEHSA-N

物化性质

• 沸点：
  548.8±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 生成 2,6-di-O-benzyl-L-lyxo-hexos-5-ulose
  参考文献：
  名称：

  Intramolecular aldol cyclization of l-lyxo-Hexos-5-ulose derivatives: A new diastereoselective synthesis of d-chiro-Inositol

  摘要：

  The DBU-promoted intramolecular aldol condensation of two partially protected L-lyxo-hexos-5-ulose derivatives (8 and 9), in turn obtained starting from methyl beta-D-galactopyrano side, takes place with fairly good yield and complete diastereoselectivity to give 2L-(2,3,6/4,5)-pentahydroxycyclohexanone derivatives, 10 and 11. The stereoselective reduction of inosose 10 with sodium triacetoxyborohydride leads, after catalytic debenzylation, to D-chiro-inositol (1), while the sodium borohydride reduction furnishes, with opposite stereoselectivity, a derivative of allo-inositol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00692-3
• 作为产物：
  描述：

  methyl 4-O-acetyl-2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranoside 在 sodium methylate 作用下， 以 吡啶 、 甲醇 、 甲苯 为溶剂， 反应 83.0h， 生成 methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-gulopyranoside
  参考文献：
  名称：

  Preparation of L-Lyxo-Hexos-5-Ulose Through C-3 Epimerization of Bis-Glycopyranosides of L-Arabino-Hexos-5-Ulose¹

  摘要：

  The unreported title compound and its 2,6-di-O-benzyl derivative have been prepared from methyl beta-D-galactopyranoside through a sequence involving the bis-glycoside methyl 2,6-di-O-benzyl-5-C-methoxy-beta-D-galactopyranoside 8, the precursor of L-arabino-hexos-5-ulose, that was converted to the L-lyxo series by inversion at C-3. The inversion was achieved in acceptable yields by selective triflation, followed by displacement with benzoate, and by an oxidation/reduction sequence. Whereas 2,5-di-O-benzyl-L-lyxo-hexos-5-ulose exists entirely as a mixture of the two anomeric 1,4-furanosic forms, the unprotected hexos-5-ulose involves at equilibrium in CD3CN/D2O at least eight tautomers, one of which is predominant.

  DOI：

  10.1080/07328309808001891

文献信息

• Bioorg. Med. Chem. Lett. 2002, 12, 3313-3315
  作者：

  DOI：——

  日期：——
• Preparation of L-<i>Lyxo</i>-Hexos-5-Ulose Through C-3 Epimerization of Bis-Glycopyranosides of L-<i>Arabino</i>-Hexos-5-Ulose¹
  作者：Pier Luigi Barili、Giancarlo Berti、Giorgio Catelani、Felicia D'Andrea、Francesco De Rensis、Giampaolo Goracci

  DOI：10.1080/07328309808001891

  日期：1998.11

  The unreported title compound and its 2,6-di-O-benzyl derivative have been prepared from methyl beta-D-galactopyranoside through a sequence involving the bis-glycoside methyl 2,6-di-O-benzyl-5-C-methoxy-beta-D-galactopyranoside 8, the precursor of L-arabino-hexos-5-ulose, that was converted to the L-lyxo series by inversion at C-3. The inversion was achieved in acceptable yields by selective triflation, followed by displacement with benzoate, and by an oxidation/reduction sequence. Whereas 2,5-di-O-benzyl-L-lyxo-hexos-5-ulose exists entirely as a mixture of the two anomeric 1,4-furanosic forms, the unprotected hexos-5-ulose involves at equilibrium in CD3CN/D2O at least eight tautomers, one of which is predominant.
• Intramolecular aldol cyclization of l-lyxo-Hexos-5-ulose derivatives: A new diastereoselective synthesis of d-chiro-Inositol
  作者：Giorgio Catelani、Antonino Corsaro、Felicia D'Andrea、Manuela Mariani、Venerando Pistarà

  DOI：10.1016/s0960-894x(02)00692-3

  日期：2002.11

  The DBU-promoted intramolecular aldol condensation of two partially protected L-lyxo-hexos-5-ulose derivatives (8 and 9), in turn obtained starting from methyl beta-D-galactopyrano side, takes place with fairly good yield and complete diastereoselectivity to give 2L-(2,3,6/4,5)-pentahydroxycyclohexanone derivatives, 10 and 11. The stereoselective reduction of inosose 10 with sodium triacetoxyborohydride leads, after catalytic debenzylation, to D-chiro-inositol (1), while the sodium borohydride reduction furnishes, with opposite stereoselectivity, a derivative of allo-inositol. (C) 2002 Elsevier Science Ltd. All rights reserved.