2-deoxy-3,4-O-isopropylidene-L-erythro-pent-1-enose propane-1,3-diyl dithioacetal | 1197349-41-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-3,4-O-isopropylidene-L-erythro-pent-1-enose propane-1,3-diyl dithioacetal
• 英文别名: [(4S,5R)-5-(1,3-dithian-2-ylidenemethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 1197349-41-9
• 化学式: C₁₁H₁₈O₃S₂
• 分子量: 262.394
• InChiKey: XCRVGTQGKKFIFK-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  89.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 2-deoxy-3,4-O-isopropylidene-L-erythro-pent-1-enose propane-1,3-diyl dithioacetal 在 2,6-di-tert-butyl-4-methylpyridine 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(5S,7R,8R) 7,8-isopropylidenedioxy-2,3,4,6,7,8-hexahydrothiopyrano[1,2-a][1,3]dithiin-5-ium trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of d- and l-erythro 1,5-dithiopent-1-enopyranoside sulfonium salts and their evaluation as glycosidase inhibitors

  摘要：

  A series of sulfonium salts derived from 1,5-dithiopent-1-enopyranosides was prepared in a three-step sequence from protected D- and L-erythrofuranoses. The key step is the nucleophilic displacement of a leaving group by a sulfur atom of carbohydrate-derived ketene dithioacetals. Such compounds were assayed for their properties as glycosidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.033
• 作为产物：
  描述：

  2,3-O-isopropylidene-L-erythrofuranose 、 2-三甲基硅基-1,3-二噻吩 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以73%的产率得到2-deoxy-3,4-O-isopropylidene-L-erythro-pent-1-enose propane-1,3-diyl dithioacetal
  参考文献：
  名称：

  Synthesis of d- and l-erythro 1,5-dithiopent-1-enopyranoside sulfonium salts and their evaluation as glycosidase inhibitors

  摘要：

  A series of sulfonium salts derived from 1,5-dithiopent-1-enopyranosides was prepared in a three-step sequence from protected D- and L-erythrofuranoses. The key step is the nucleophilic displacement of a leaving group by a sulfur atom of carbohydrate-derived ketene dithioacetals. Such compounds were assayed for their properties as glycosidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.033

文献信息

• Synthesis of d- and l-erythro 1,5-dithiopent-1-enopyranoside sulfonium salts and their evaluation as glycosidase inhibitors
  作者：Marie Buchotte、Claudia Bello、Pierre Vogel、Nicolas Floquet、Murielle Muzard、Richard Plantier-Royon

  DOI：10.1016/j.tetasy.2009.07.033

  日期：2009.9

  A series of sulfonium salts derived from 1,5-dithiopent-1-enopyranosides was prepared in a three-step sequence from protected D- and L-erythrofuranoses. The key step is the nucleophilic displacement of a leaving group by a sulfur atom of carbohydrate-derived ketene dithioacetals. Such compounds were assayed for their properties as glycosidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.