(4R)-hydroxymethyl-4-thiobutyro-1,4-lactone | 185303-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (4R)-hydroxymethyl-4-thiobutyro-1,4-lactone
• 英文别名: (R)-5-(hydroxymethyl)thiolan-2-one；(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone；(5R)-5-(hydroxymethyl)thiolan-2-one
• CAS: 185303-62-2
• 化学式: C₅H₈O₂S
• 分子量: 132.183
• InChiKey: GTDYKMLEBWRLMJ-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  叔丁基二苯基氯硅烷 、 (4R)-hydroxymethyl-4-thiobutyro-1,4-lactone 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (4R)-4-(tert-butyldiphenylsilyloxymethyl)-4-thiobutyro-1,4-lactone
  参考文献：
  名称：

  2-（叔丁基二甲基甲硅烷氧基）噻吩：在2'，3'-二脱氧-4'-硫胞苷的两种对映体的总合成中的应用

  摘要：

  利用新型2-（叔丁基二甲基甲硅烷氧基）噻吩（1，TBSOT）作为通用的碳亲核试剂和甘油醛丙酮化物的两种对映体作为手性来源，这两种抗HIV活性2'，3'-dideoxy-4'-的对映体均进入设计并执行了硫胞苷10和ent-10 。

  DOI：

  10.1016/0040-4039(95)00162-6
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 吡啶 、 盐酸 、 sodium 、 硫脲 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 118.83h， 生成 (4R)-hydroxymethyl-4-thiobutyro-1,4-lactone
  参考文献：
  名称：

  Two approaches to the enantioselective synthesis of (4R)-(−)-4-hydroxymethyl-4-thiobutyro-1,4-lactone

  摘要：

  Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first approach was the SmI2-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from 1. The other strategy, which starts from 6, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (8) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave 12 (40% overall yield from 8). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00568-6

文献信息

• Expeditious Syntheses of Sugar-Modified Nucleosides and Collections Thereof Exploiting Furan-, Pyrrole-, and Thiophene-Based Siloxy Dienes
  作者：Gloria Rassu、Franca Zanardi、Lucia Battistini、Enrico Gaetani、Giovanni Casiraghi

  DOI：10.1021/jm960400q

  日期：1997.1.1

  enriched 2',3'-dideoxynucleosides 14a-c (alpha and beta anomers of L- and D-series), 2',3'-dideoxy-4'-thionucleosides 21a-c (alpha and beta anomers of L- and D-series), and 2',3'-dideoxy-4'-azanucleosides 28a-c (beta anomers of L- and D-series) were synthesized, with uniform chemistry and high stereochemical efficiency, exploiting a triad of versatile heterocyclic siloxy dienes, namely, 2-(tert-but

  一系列单独的糖修饰的嘧啶核苷，包括对映体富集的2'，3'-二脱氧核苷14a-c（L和D系列的α和β端基异构体），2'，3'-二脱氧-4'-硫代核苷21a-合成了c（L和D系列的α和β端基异构体）和2'，3'-二脱氧-4'-氮杂核苷28a-c（L和D系列的β端基异构体）立体化学效率，利用三元组的多功能杂环甲硅烷氧基二烯，即2-（叔丁基二甲基甲硅烷氧基）呋喃（TBSOF），2-（叔丁基二甲基甲硅烷氧基）噻吩（TBSOT）和N-（叔丁氧基羰基）-2-（叔丁基二甲基甲硅烷氧基）吡咯（TBSOP）。合成方法有利地使用甘油醛丙酮化物的对映体（D-1和L-1）作为手性来源和甲酰基阳离子的合成等同物。
• 2-(tert-butyldimethylsiloxy)thiophene: Application to total syntheses of both enantiomers of 2′,3′-dideoxy-4′-thiocytidine
  作者：Gloria Rassu、Pietro Spanu、Luigi Pinna、Franca Zanardi、Giovanni Casiraghi

  DOI：10.1016/0040-4039(95)00162-6

  日期：1995.3

  Exploiting novel 2-(tert-butyldimethylsiloxy)thiophene (1, TBSOT) as versatile carbon nucleophile and both enantiomers of glyceraldehyde acetonide as chiral sources, an entry to both enantiomers of anti HIV-active 2′,3′-dideoxy-4′-thiocytidine 10 and ent-10 was devised and executed.

  利用新型2-（叔丁基二甲基甲硅烷氧基）噻吩（1，TBSOT）作为通用的碳亲核试剂和甘油醛丙酮化物的两种对映体作为手性来源，这两种抗HIV活性2'，3'-dideoxy-4'-的对映体均进入设计并执行了硫胞苷10和ent-10 。
• Two approaches to the enantioselective synthesis of (4R)-(−)-4-hydroxymethyl-4-thiobutyro-1,4-lactone
  作者：Patricia A Zunszain、Oscar Varela

  DOI：10.1016/s0957-4166(99)00568-6

  日期：2000.2

  Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first approach was the SmI2-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from 1. The other strategy, which starts from 6, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (8) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave 12 (40% overall yield from 8). (C) 2000 Elsevier Science Ltd. All rights reserved.