L-arabinose dibenzyl dithioacetal | 40733-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-arabinose dibenzyl dithioacetal
• 英文别名: Arabinose dibenzyl dithioacetal；L-arabinose dibenzyl thioacetal；L-Arabinose-dibenzyldithioacetal；L-Arabinose-dibenzylmercaptal；(2S,3S,4R)-5,5-bis(benzylsulfanyl)pentane-1,2,3,4-tetrol
• CAS: 40733-11-7
• 化学式: C₁₉H₂₄O₄S₂
• 分子量: 380.529
• InChiKey: BEZCZIJEWKDEGU-OKZBNKHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-arabinose dibenzyl dithioacetal 在 甲醇 、 mercury dichloride 作用下， 生成 甲基-L-吡喃阿拉伯糖苷
  参考文献：
  名称：

  Pacsu; Ticharich, Chemische Berichte, 1929, vol. 62, p. 3008,3011

  摘要：

  DOI：
• 作为产物：
  描述：

  L-阿拉伯糖 、 苄硫醇 在 盐酸 作用下， 以88%的产率得到L-arabinose dibenzyl dithioacetal
  参考文献：
  名称：

  使用新型[2,3] wittig重排，立体控制合成两性霉素B的AC 14 -C 20结构单元

  摘要：

  由L-阿拉伯糖以13个步骤合成多烯大环内酯抗生素两性霉素B（1）的C 1 4 -C 20单元11。关键步骤7→10的特点是通过新颖[23]的维蒂格重排中的不对称感应进行非对映控制。

  DOI：

  10.1016/s0040-4039(00)82180-2

文献信息

• New synthesis of both D- and L-3-O-carbamoyl-2-deoxy-4-thioribosides, substrates for β-selective glycosylations
  作者：Sue Shaw-Ponter、Peter Rider、Robert J. Young

  DOI：10.1016/0040-4039(96)00139-6

  日期：1996.3

  A new route to intermediates for the synthesis of 2′-deoxy-4′-thionucleosides is described. By utilising enantiomeric erythro-dibenzyldithioacetals, both D- and L-3-O-(N-acyl)carbamoyl thiosugars, which give β-selective glycosylations, are radily produced.

  描述了合成2'-脱氧-4'-硫代核苷的中间体的新途径。通过利用对映异构的赤型-二苄基二硫缩醛，放射状地产生D-和L-3- O-（N-酰基）氨基甲酰基硫糖基，它们产生β-选择性的糖基化。
• Short synthesis of hydroxylated thiolane and selenolane rings from mono-benzylated pentitols and aldoses dithioacetals bis-thionocarbonates as bis-electrophilic substrates
  作者：Alain Danquigny、Mohamed Aït Amer Meziane、Gilles Demailly、Mohammed Benazza

  DOI：10.1016/j.tet.2005.05.008

  日期：2005.7

  by reaction with diimidazolyl thione (Im2CS) in 1,4-dioxane. These bis-electrophilic adducts react regioselectively with Na2S·9H2O or Se/NaBH4 to lead regioselectively to the corresponding thiolane and selenolane rings in good yields for a short synthesis (47–65%).

  1- O-苄基戊糖醇（具有d-阿拉伯糖，d- lyxo，d，l-木糖和d，l-核糖构型）和醛糖二苄基二硫缩醛（具有l-阿拉伯糖，d- lyxo，d-木糖，d-核糖，d -半乳糖，D-葡萄糖和D-甘露配置）通过与二咪唑基硫酮（IM反应中直接和有效地转化为它们的环状二硫代羰基碳酸衍生物（61-73％）2在1,4-二恶烷CS）。这些双亲电子加合物与Na 2 S·9H 2 O或Se / NaBH发生区域选择性反应4可以短区域合成（47–65％），以良好的产率将区域选择性地引入相应的硫杂环戊烷和亚硒烷环。
• 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
  作者：Alain Danquigny、Mohammed Benazza、Sylvain Protois、Gilles Demailly

  DOI：10.1016/j.tetlet.2004.03.197

  日期：2004.5

  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.
• Synthesis of 5-thialdopentopyranoside via dithioacetal rearrangement and glycosidation to give pseudodisaccharides
  作者：Carole Lépine、Caroline Roy、Daniel Delorme

  DOI：10.1016/s0040-4039(00)73176-5

  日期：1994.3

  Rearrangement of acetylated 5-O-p-toluenesulfonyl-L-arabinose dibenzyl dithioacetal 10 gave benzyl 1,5-dithio-L-arabinopyranoside 6 which upon anomeric bromination followed by glycosidation led to pseudodisaccharide 20 containing a sulfur atom in the ring of the non-reducing unit Similarly, benzyl 1,5-dithio-D-lyxopyranoside 17 was obtained from 5-O-p-tolueresulfonyl-D-lyxose dibenzyl dithioacetal 16.
• Machiya, Kozo; Ichimoto,Itsuo; Kirihata, Mitsunori, Agricultural and Biological Chemistry, 1985, vol. 49, # 3, p. 643 - 650
  作者：Machiya, Kozo、Ichimoto,Itsuo、Kirihata, Mitsunori、Ueda, Hiroo

  DOI：——

  日期：——