2,6-di-O-benzyl-L-lyxo-hexos-5-ulose | 497162-80-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-di-O-benzyl-L-lyxo-hexos-5-ulose
• 英文别名: (2R,3R,4R)-3,4-dihydroxy-5-oxo-2,6-bis(phenylmethoxy)hexanal
• CAS: 497162-80-8
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: RCBDSWUCZNVJLR-UFYCRDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-di-O-benzyl-L-lyxo-hexos-5-ulose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 2,4-di-O-benzyl-2L-(2,3,4,5,6)-pentahydroxycyclohexanone
  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-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

文献信息

• Toward the synthesis of fine chemicals from lactose: preparation of d-xylo and l-lyxo-aldohexos-5-ulose derivatives
  作者：Giorgio Catelani、Felicia D’Andrea、Lorenzo Guazzelli、Venerando Pistarà

  DOI：10.1016/j.carres.2009.01.014

  日期：2009.4

  The transformation of (5R)-2,6-di-O-benzyl-5-C-methoxy-beta-D-galactopyranosyl-(1 -> 4)-2,3:5,6-di-O-iso-propylidene-aldehydo-D-glucose dimethyl acetal (8) into partially protected derivatives of D-xylo- and L-lyxo-aldohexos-5-ulose has been reported, applying appropriate epimerisation methods to its 3'-O- and 4'-O-protected alcoholic derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
• Bioorg. Med. Chem. Lett. 2002, 12, 3313-3315
  作者：

  DOI：——

  日期：——
• 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.