D-Glucose-dibenzyldithioacetal | 6936-67-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-Glucose-dibenzyldithioacetal
• 英文别名: D-Glucose-dibenzyl-dithioacetal；(2R,3R,4S,5R)-6,6-bis(benzylsulfanyl)hexane-1,2,3,4,5-pentol
• CAS: 6936-67-0
• 化学式: C₂₀H₂₆O₅S₂
• 分子量: 410.555
• InChiKey: XYJQPBTZELOVDP-AKHDSKFASA-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：

  D-Glucose-dibenzyldithioacetal 在 甲醇 、 mercury dichloride 作用下， 生成 alpha-甲基葡萄糖甙
  参考文献：
  名称：

  Pacsu, Chemische Berichte, 1925, vol. 58, p. 509,512

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 D-Glucose-dibenzyldithioacetal
  参考文献：
  名称：

  Stanek; Sada, Collection of Czechoslovak Chemical Communications, 1949, vol. 14, p. 540,546

  摘要：

  DOI：

文献信息

• Epimerization of Monosaccharides Under Acetolysis Conditions
  作者：Walter Sowa

  DOI：10.1139/v71-548

  日期：1971.10.15

  Monosaccharides with a cis-configuration at C-2 and -3 readily undergo inversion at C-2 in an acetolysis medium composed of acetic acid, acetic anhydride, and sulfuric acid. The acetolysis-inversion reaction has been carried out with 2,3;5,6-di-O-isopropylidene-D-gulofuranose, 2,3;6,7-di-O-isopropylidene-D-glycero-D-gulo-heptose, 2,3-O-isopropylidene-D-ribose, D-ribose, and D-mannose using chromatography for isolation of the deacetylated epimeric products. The reaction requires a medium with a high concentration of acetic acid (ca. 90%) and appears to take place only with furanose structures. Inversions observed with the unsubstituted pyranoses D-ribose and D-mannose probably occur because of tautomerization to furanose forms. The epimerization proceeds in the direction which yields a smaller number of cis-oriented groups at C-2, -3, and -4 of the furanose forms of monosaccharides.

  在C-2和-3位置具有顺式构型的单糖在由乙酸、乙酸酐和硫酸组成的乙酰化介质中很容易在C-2位置发生倒位反应。使用色谱法分离去乙酰化的对映产物，已经对2,3;5,6-二-O-异丙基-D-古洛呋喃糖、2,3;6,7-二-O-异丙基-D-甘露-D-古庚糖、2,3-O-异丙基-D-核糖、D-核糖和D-甘露糖进行了乙酰化-倒位反应。该反应需要含有高浓度乙酸（约90%）的介质，并且似乎只发生在呋喃糖结构中。未取代的吡喃糖D-核糖和D-甘露糖观察到的倒位可能是因为互变异构为呋喃糖形式。对映异构化朝着使单糖呋喃糖形式的C-2、-3和-4位置具有较少顺式取向基团的方向进行。
• 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.
• Lieser; Schweizer, Justus Liebigs Annalen der Chemie, 1935, vol. 519, p. 271,277
  作者：Lieser、Schweizer

  DOI：——

  日期：——
• Glycofuranosides and Thioglycofuranosides. I. A Method of Preparation and its Application to Galactose and Glucose
  作者：John W. Green、Eugene Pacsu

  DOI：10.1021/ja01286a015

  日期：1937.7