L-Altrose-dibenzyldithioacetal | 61865-75-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-Altrose-dibenzyldithioacetal
• 英文别名: (2S,3S,4S,5R)-6,6-bis(benzylsulfanyl)hexane-1,2,3,4,5-pentol
• CAS: 61865-75-6
• 化学式: C₂₀H₂₆O₅S₂
• 分子量: 410.555
• InChiKey: XYJQPBTZELOVDP-CADBVGFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  152
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  L-Altrose-dibenzyldithioacetal 、 N,N'-硫羰基二咪唑 以 1,4-二氧六环 为溶剂， 以65%的产率得到2,3:5,6-di-O-thiocarbonyl-D-galactose dibenzyl dithioacetal
  参考文献：
  名称：

  Versatile use of bis-cyclic thionocarbonates of polyols as bis-electrophilic intermediates. Synthesis of polyhydroxylated thioanhydropentitols with d,l-arabino, l-ribo and l-xylo, and thioanhydroaldoses with d-lyxo, l-ribo, d-xylo, d-allo, d-gulo and d-altro configurations

  摘要：

  1-O-Benzylpentitols (with D-arabino, D-, D,L-xylo and D,L-ribo configurations) and aldose dibenzyldithioacetals (with L-arabino, D-lyxo, D-xylo, D-ribo, D-galacto, D-gluco and D-manno configurations) were directly and efficiently transformed into their cyclic bis-thionocarbonate derivatives (61-73%) by reaction with diimidazolyl thione (Im(2)CS) in 1,4-dioxane. These bis-electrophilic adducts react regioselectively with Na2S-9H(2)O to lead to 1,4-, 2,5- or 3,6-thioanhydroalditol derivatives in good yields (47-65%). Thioanhydro configurations D,L-arabino, L-ribo and L-xylo from pentitols, and D-lyxo, L-ribo, D-xylo, D-allo, D-gulo and D-altro from aldoses were obtained. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.197
• 作为产物：
  描述：

  L-阿卓糖 、 苄硫醇 在 盐酸 作用下， 生成 L-Altrose-dibenzyldithioacetal
  参考文献：
  名称：

  The Rearrangement of Sugar Acetates by Aluminum Chloride. Further Studies on Neolactose and d-Altrose¹

  摘要：

  DOI：

  10.1021/ja01312a066