5-desoxy-5-thio-D-xylopyranose | 1910-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 5-desoxy-5-thio-D-xylopyranose
• 英文别名: 5-thio-D-xylopyranose；(3R,4S,5S)-thiane-2,3,4,5-tetrol
• CAS: 1910-72-1
• 化学式: C₅H₁₀O₄S
• 分子量: 166.198
• InChiKey: QWVJFKXOINHVGD-IOVATXLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-desoxy-5-thio-D-xylopyranose 在 吡啶 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 ethyl (2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl)acetate
  参考文献：
  名称：

  New 1-C-(5-thio-d-xylopyranosyl) derivatives as potential orally active venous antithrombotics

  摘要：

  In the search for new orally active antithrombotic drugs that are metabolically stable, we explored the synthesis of 1-C-(5-thio-D-xylosyl) derivatives, examining radical and nucleophilic methods. Thus synthesized were aryl, benzyl, alkylcarboxymethylenyl, arylsulfonylmethylenyl and alkylaminocarboxymethylenyl C-linked analogues of 5-thio-D-xylopyranosides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00147-2
• 作为产物：
  描述：

  5-thio-D-xylulofuranose 在 sodium hydroxide 、 磷酸 作用下， 以 various solvent(s) 为溶剂， 反应 192.0h， 生成 5-desoxy-5-thio-D-xylopyranose
  参考文献：
  名称：

  5-硫代-D-吡喃木糖的化学酶法合成

  摘要：

  5-硫代-D-吡喃木糖是一种用于制备具有抗血栓形成活性的药物的合成子，它是通过相应的酮糖、5-硫代-D-呋喃木糖和葡萄糖异构酶的酶促异构化合成的。该化合物是通过两种不同的化学酶促途径获得的，关键步骤是立体有择地形成 C-C 键，由转酮醇酶或果糖-1,6-二磷酸醛缩酶催化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600627

文献信息

• Stereoselective U-4CRs with 1-amino-5-desoxy-5-thio-2,3,4-O-isobutanoyl-β-d-xylopyranose—an effective and selectively removable chiral auxiliary
  作者：Günther F Ross、Eberhardt Herdtweck、Ivar Ugi

  DOI：10.1016/s0040-4020(02)00484-2

  日期：2002.7

  The Ugi four component reaction (U-4CR) offers a short and direct route for the synthesis of α-amino acid and peptide derivatives. With 1-amino-5-desoxy-5-thio-2,3,4-O-isobutanoyl-β-d-xylopyranose as a chiral amine component excellent chemical yields and stereoselectivities are obtained. After the U-4CR the chiral auxiliary can be cleaved off selectively under mild conditions. The configuration of

  Ugi四组分反应（U-4CR）为合成α-氨基酸和肽衍生物提供了一条短而直接的途径。用1-氨基-5-脱氧-5-硫代2,3,4- O-异丁酰基-β-d-吡喃吡喃糖作为手性胺组分，可获得优异的化学产率和立体选择性。在U-4CR之后，可以在温和条件下选择性地裂解手性助剂。通过X射线分析确认了其中一种产品的构型。
• Stereoselective syntheses of α-amino acid and peptide derivatives by the U-4CR of 5-desoxy-5-thio-<small>D</small>-xylopyranosylamine
  作者：Günther Ross、Ivar Ugi

  DOI：10.1139/cjc-79-12-1934

  日期：——

  Since 1961, the synthesis of alpha-amino acids derivatives by the four-component reaction of isocyanides (U-4CR) as a one-pot reaction has been developed. Only recently it was found that a variety of these cc-amino acids compounds can be formed stereoselectively by the U-4CR using 1-amino-5-deoxy-5-thio-2,3,4-tri-O-isobutanoyl-beta-D-xylopyranose as the amine component. The stereoselectivity inducing auxiliary 5-desoxy-5-thio-D-xylopyranosyl group of the so-formed products can be replaced selectively by hydrogen.
• Chemoenzymatic Synthesis of 5-Thio-D-xylopyranose
  作者：Franck Charmantray、Philippe Dellis、Virgil Hélaine、Soth Samreth、Laurence Hecquet

  DOI：10.1002/ejoc.200600627

  日期：2006.12

  5-thio-D-xylopyranose, a synthon used for the preparation of drugs with antithrombotic activity, was synthesised by an enzymatic isomerisation from the corresponding ketose, 5-thio-D-xylulofuranose, with glucose isomerase. This compound was obtained by two different chemoenzymatic routes, the key step being the stereospecific formation of a C–C bond, catalysed by transketolase or fructose-1,6-bisphosphate

  5-硫代-D-吡喃木糖是一种用于制备具有抗血栓形成活性的药物的合成子，它是通过相应的酮糖、5-硫代-D-呋喃木糖和葡萄糖异构酶的酶促异构化合成的。该化合物是通过两种不同的化学酶促途径获得的，关键步骤是立体有择地形成 C-C 键，由转酮醇酶或果糖-1,6-二磷酸醛缩酶催化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• New 1-C-(5-thio-d-xylopyranosyl) derivatives as potential orally active venous antithrombotics
  作者：Laurent Mignon、Christophe Goichot、Philippe Ratel、Gérald Cagnin、Michel Baudry、Jean-Pierre Praly、Benaı̈ssa Boubia、Véronique Barberousse

  DOI：10.1016/s0008-6215(03)00147-2

  日期：2003.6

  In the search for new orally active antithrombotic drugs that are metabolically stable, we explored the synthesis of 1-C-(5-thio-D-xylosyl) derivatives, examining radical and nucleophilic methods. Thus synthesized were aryl, benzyl, alkylcarboxymethylenyl, arylsulfonylmethylenyl and alkylaminocarboxymethylenyl C-linked analogues of 5-thio-D-xylopyranosides. (C) 2003 Elsevier Science Ltd. All rights reserved.