2,3,5-tri-O-benzyl-D-arabino-1,4-thiolactone | 141118-01-6

• 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: 2,3,5-tri-O-benzyl-D-arabino-1,4-thiolactone
• 英文别名: (3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane-2-thione
• CAS: 141118-01-6
• 化学式: C₂₆H₂₆O₄S
• 分子量: 434.556
• InChiKey: HRTXVDLEJJFKCB-SDHSZQHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3S,4R,5R)-2-(benzenesulfinylsulfanyl)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane 在 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以84%的产率得到2,3,5-tri-O-benzyl-D-arabino-1,4-thiolactone
  参考文献：
  名称：

  Efficient synthesis of carbohydrate thionolactones

  摘要：

  Carbohydrate thionolactones may be efficiently synthesized from the corresponding 1-thio sugars via a two-step procedure involving formation of a glycosyl phenylthiosulfinate by treatment with either phenylsulfinyl chloride or 1-(phenylsulfinyl)piperidine (BSP), and subsequent thermal elimination in toluene. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.104

文献信息

• One-pot synthesis of carbohydrate thionolactones from 1-thiosugars
  作者：Brendan L. Wilkinson、Antony J. Fairbanks

  DOI：10.1016/j.tetlet.2008.05.145

  日期：2008.8

  commercially available tert-butylsulfinyl chloride in toluene at room temperature, followed by thermolysis. The method can also be used to generate reactive thioaldehydes and thioketones directly from thiols, which can be trapped in situ with a suitable diene.

  为碳水化合物thionolactones的从合成的一般和高效的一锅法相应的1- thiosugar是描述涉及一中间的糖基的形成小号-叔丁基硫代亚磺酸酯在原位治疗与市售硫醇的叔丁基亚磺酰氯在室温下甲苯，然后热解。该方法还可用于直接从硫醇生成反应性硫醛和硫酮，这些硫醇和硫酮可用合适的二烯就地捕获。
• Redox glycosidation: stereoselective syntheses of (1.fwdarw.6) linked disaccharides via thionoester intermediates
  作者：Anthony G. M. Barrett、Albert C. Lee

  DOI：10.1021/jo00036a012

  日期：1992.5

  Perbenzyl derivatives of the disaccharides benzyl 6-O-(alpha(and beta)-D-glucopyranosyl)-alpha-D-galactopyranoside and benzyl 6-O-(alpha(and beta)-D-mannopyranosyl)-alpha-D-galactopyranoside were each prepared in a stereoselective manner by acylation, thionation, and reductive desulfurization. The use of 2,4-bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (4b) as a mild thionation reagent for esters and lactones is also described.