2(S)-(hydroxymethyl)-1,3-oxathiolane | 173841-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环戊烷
• 英文名称: 2(S)-(hydroxymethyl)-1,3-oxathiolane
• 英文别名: 2S-hydroxymethyl-1,3-oxathiolane；[(2S)-1,3-oxathiolan-2-yl]methanol
• CAS: 173841-91-3
• 化学式: C₄H₈O₂S
• 分子量: 120.172
• InChiKey: CHFYSOCPHBZWAG-BYPYZUCNSA-N

物化性质

• 沸点：
  245.8±25.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 2(S)-(hydroxymethyl)-1,3-oxathiolane 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以44.6%的产率得到2(S)-(benzoyloxymethyl)-1,3-oxathiolane
  参考文献：
  名称：

  Process for Manufacture of Optically Active 2-(Acyloxymethyl)-1,3-Oxathiolanes

  摘要：

  提供了一种制备光学活性的Formula I的2-(酰氧甲基)-1,3-噁硫杂环己烷的方法，包括制备一个外消旋化合物和酶催化的对映异构体的动力学拆分。该发明还可以提供对酶催化反应的副产物进行酯化和外消旋化的方法。通过这种方式，制备了2(R)-(苯甲酰氧甲基)-1,3-噁硫杂环己烷，用作制造抗HIV药物Apricitabine的有用中间体。

  公开号：

  US20120157693A1
• 作为产物：
  描述：

  (1'R,2'S,5'R)-menthyl-1,3-oxathiolan-2S-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2(S)-(hydroxymethyl)-1,3-oxathiolane
  参考文献：
  名称：

  通过还原-氧化过程将手性氧杂硫杂环戊烷上的离去基团转位，合成旋光的2'，3'-二脱氧-3'-oxa-4'-硫代-核糖核苷类似物

  摘要：

  据报道具有独特结构特征的手性核苷类似物的合成。该策略基于还原性氧化过程，以完成具有已知构型的手性草硫杂环戊烷中离去基团的转座。

  DOI：

  10.1016/s0040-4039(00)76955-3

文献信息

• Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with
  申请人：BioChem Pharma, Inc.

  公开号：US05587480A1

  公开（公告）日：1996-12-24

  This invention relates to novel substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes or pharmaceutically acceptable salts and esters thereof, of the formula: ##STR1## wherein X is S, S.dbd.O, or SO.sub.2 ; Y is O, S, S.dbd.O, or SO.sub.2 ; R.sub.1 is hydrogen, trisubstituted silyl, C.sub.1-6 alkyl, aralkyl, or C.sub.1-6 acyl, and R.sub.2 is a pyrimidine base or an analogue or derivative thereof. This invention also relates to processes for preparing these compounds, intermediates useful in their preparation, to pharmaceutical compositions containing them and to the use of these compounds as antiviral agents.

  这项发明涉及新颖的取代1,3-噻烷和取代1,3-二硫烷或其药用盐和酯，化学式如下：##STR1## 其中X为S、S.dbd.O或SO.sub.2；Y为O、S、S.dbd.O或SO.sub.2；R.sub.1为氢、三取代硅基、C.sub.1-6烷基、芳基烷基或C.sub.1-6酰基，R.sub.2为嘧啶碱基或其类似物或衍生物。这项发明还涉及制备这些化合物的方法，用于制备它们的中间体，含有它们的药物组合物以及将这些化合物用作抗病毒剂的用途。
• Substituted 1,3-oxathiolanes with antiviral properties
  申请人：BioChem Pharma, Inc.

  公开号：US06369066B1

  公开（公告）日：2002-04-09

  This invention relates to single enantiomers of novel cis-substituted 1,3-oxathiolanes, of the formula (I): wherein; R1 is hydrogen, and R2 is cytosine or 5-fluorocytosine; and pharmaceutically acceptable salts and esters thereof. This invention also relates to pharmaceutical compositions containing them and to the use of these compounds as antiviral agents, particularly in combination therapy.

  这项发明涉及一种新型顺式取代的单对映体1,3-噁硫环己烷，化学式为（I）：其中；R1为氢，R2为胞嘧啶或5-氟胞嘧啶；以及其药学上可接受的盐和酯。这项发明还涉及含有它们的药物组合物，以及将这些化合物用作抗病毒剂，特别是在联合疗法中的用途。
• Process for manufacture of optically active 2-(acyloxymethyl)-1,3-oxathiolanes using enzymatic resolution
  申请人：Thesis Chemistry, LLC

  公开号：US08153416B2

  公开（公告）日：2012-04-10

  There is provided a process for manufacture of optically-active, 2-(acyloxymethyl)-1,3-oxathiolanes of Formula I comprising a preparation of a racemic compound and an enzyme-catalyzed kinetic resolution of the enantiomers. The invention may further provide for the esterification and racemization of the by-product of the enzymatic reaction. In this manner, 2(R)-(benzoyloxymethyl)-1,3-oxathiolane is prepared as a useful intermediate for manufacture of the anti-HIV drug Apricitabine.

  提供了一种制备光学活性的Formula I的2-(acyloxymethyl)-1,3-oxathiolanes的方法，包括制备外消旋化合物和酶催化的对映体动力学分辨。该发明还可以进一步提供对酶促反应的副产物进行酯化和外消旋化的方法。通过这种方式，制备出2(R)-(benzoyloxymethyl)-1,3-oxathiolane，作为制备抗HIV药物Apricitabine的有用中间体。
• Process for manufacture of optically active 2-(acyloxymethyl)-1,3-oxathiolanes
  申请人：Peterson John R.

  公开号：US08354546B2

  公开（公告）日：2013-01-15

  There is provided a process for manufacture of optically-active, 2-(acyloxymethyl)-1,3-oxathiolanes of Formula I comprising a preparation of a racemic compound and an enzyme-catalyzed kinetic resolution of the enantiomers. The invention may further provide for the esterification and racemization of the by-product of the enzymatic reaction. In this manner, 2(R)-(benzoyloxymethyl)-1,3-oxathiolane is prepared as a useful intermediate for manufacture of the anti-HIV drug Apricitabine.

  提供了一种制造光学活性的Formula I的2-(酰氧甲基)-1,3-噁二唑烷的工艺，包括制备外消旋化合物和酶催化的对映体动力学分辨。本发明还可以提供酯化和酶催化反应副产物的消旋化。通过这种方式，制备了2(R)-(苯甲酰氧甲基)-1,3-噁二唑烷，用于制造抗HIV药物Apricitabine的有用中间体。
• Synthesis of optically active 2′,3′-dideoxy-3′-oxa-4′-thio-ribonucleoside analogues by transposition of a leaving group on chiral oxathiolanes via a reductive-oxidative process
  作者：Wei Wang、Haolun Jin、Tarek S. Mansour

  DOI：10.1016/s0040-4039(00)76955-3

  日期：1994.7

  The synthesis of chiral nucleoside analogues with a unique structural feature is reported. The strategy is based on a reductive-oxidative process to complete the transposition of the leaving group in chiral oxathiolanes with known configuration.

  据报道具有独特结构特征的手性核苷类似物的合成。该策略基于还原性氧化过程，以完成具有已知构型的手性草硫杂环戊烷中离去基团的转座。