(2R,3R,4S,5R,6R)-2,6-dimethoxy-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-4-ol | 497162-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-2,6-dimethoxy-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-4-ol
• CAS: 497162-79-5
• 化学式: C₂₉H₃₄O₇
• 分子量: 494.585
• InChiKey: HHNZBUQBTVKTLK-MMBNBZRISA-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：

  (2R,3R,4S,5R,6R)-2,6-dimethoxy-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-4-ol 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 (2R,3S,4S,5S,6S)-2,4,6-Tris-benzyloxy-3,5-dihydroxy-cyclohexanone
  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 2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranoside 在 sodium tetrahydroborate 、 四丙基高钌酸铵 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R,4S,5R,6R)-2,6-dimethoxy-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-4-ol
  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

文献信息

• 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.