Acetic acid (2S,3S,4R,5S)-5-acetoxy-3-acetylamino-2-methoxy-tetrahydro-thiopyran-4-yl ester | 192517-61-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: Acetic acid (2S,3S,4R,5S)-5-acetoxy-3-acetylamino-2-methoxy-tetrahydro-thiopyran-4-yl ester
• CAS: 192517-61-6
• 化学式: C₁₂H₁₉NO₆S
• 分子量: 305.352
• InChiKey: XDGKLFQONRMQFO-RHYQMDGZSA-N

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4R,5S)-5-acetoxy-3-acetylamino-2-methoxy-tetrahydro-thiopyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到N-((2S,3S,4R,5S)-4,5-Dihydroxy-2-methoxy-tetrahydro-thiopyran-3-yl)-acetamide
  参考文献：
  名称：

  Synthesis of 4-cyanophenyl 2-azido-2-deoxy- and 3-azido-3-deoxy-1,5-dithio-β-d-xylopyranosides

  摘要：

  Azidonitration of 3,4-di-O-benzoyl-1,5-anhydro-5-thio-D-threo-pent-1-enitol (3,4-di-O-benzoyl-5-thio-D-xylal) afforded a I:1 mixture of 2-azido-3,4-di-O-benzoyl-2-deoxy-1-O-nitro-5-thio-alpha-D-xylo- and lyxo-pyranosides, which were converted after separation into their 1-O-acetyl derivatives 8 and 11, respectively. Glycosidation of 8 and 11 with methanol in the presence of trimethylsilyl triflate afforded methyl 2-azido-3,4-di-O-benzoyl-2-deoxy-5-thio-alpha,beta-D-xylo- and lyxo-pyranosides in a ratio of 1:I, and 5:2, respectively. When 4-cyanothiophenol was used as acceptor for the glycosidation of 8, the anomeric thioglycosides were formed in the same ratio (1:1). Deacetylation of the beta-isomer afforded 4-cyanophenyl 2-azido-2-deoxy-1,5-dithio-beta-lxyo-pyranoside 3. 3-Azido-3-deoxy-5-S-benzoyl-1,2-O-isopropylidene-alpha-D-xylofuranose was synthesised from D-glucose in 10 steps and was converted into 1,2,4-tri-O-acetyl-3-azido-3-deoxy-5-thio-D-xylopyranose 31. Glycosidation of 31 with 4-cyanothiophenol in the presence of trimethylsilyl triflate afforded 4-cyanothiophenyl 2,4-di-O-acetyl-3-azido-3-deoxy-5-thio-alpha,beta-D-xylopyranoside in a ratio of 1:1.5. Their deacetylation gave 4-cyanophenyl 3-azido-3-deoxy-1,5-dithio-beta-D-xylopyranoside 4 and its alpha-anomer 34. Reduction of 4 with sodium borohydride-nickel chloride gave the 3-amino derivative 36, which was converted into the acetamido compound 38. Compounds 3, 3, and 36 possess high oral antithrombotic activity, which decreases on acetylation of the amino group in 38. The alpha-anomer 34 was inactive. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00079-7
• 作为产物：
  描述：

  (3S,4R,5S)-5-Azido-6-methoxy-tetrahydro-thiopyran-3,4-diol 在 吡啶 、 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 Acetic acid (2S,3S,4R,5S)-5-acetoxy-3-acetylamino-2-methoxy-tetrahydro-thiopyran-4-yl ester
  参考文献：
  名称：

  Synthesis of 4-cyanophenyl 2-azido-2-deoxy- and 3-azido-3-deoxy-1,5-dithio-β-d-xylopyranosides

  摘要：

  Azidonitration of 3,4-di-O-benzoyl-1,5-anhydro-5-thio-D-threo-pent-1-enitol (3,4-di-O-benzoyl-5-thio-D-xylal) afforded a I:1 mixture of 2-azido-3,4-di-O-benzoyl-2-deoxy-1-O-nitro-5-thio-alpha-D-xylo- and lyxo-pyranosides, which were converted after separation into their 1-O-acetyl derivatives 8 and 11, respectively. Glycosidation of 8 and 11 with methanol in the presence of trimethylsilyl triflate afforded methyl 2-azido-3,4-di-O-benzoyl-2-deoxy-5-thio-alpha,beta-D-xylo- and lyxo-pyranosides in a ratio of 1:I, and 5:2, respectively. When 4-cyanothiophenol was used as acceptor for the glycosidation of 8, the anomeric thioglycosides were formed in the same ratio (1:1). Deacetylation of the beta-isomer afforded 4-cyanophenyl 2-azido-2-deoxy-1,5-dithio-beta-lxyo-pyranoside 3. 3-Azido-3-deoxy-5-S-benzoyl-1,2-O-isopropylidene-alpha-D-xylofuranose was synthesised from D-glucose in 10 steps and was converted into 1,2,4-tri-O-acetyl-3-azido-3-deoxy-5-thio-D-xylopyranose 31. Glycosidation of 31 with 4-cyanothiophenol in the presence of trimethylsilyl triflate afforded 4-cyanothiophenyl 2,4-di-O-acetyl-3-azido-3-deoxy-5-thio-alpha,beta-D-xylopyranoside in a ratio of 1:1.5. Their deacetylation gave 4-cyanophenyl 3-azido-3-deoxy-1,5-dithio-beta-D-xylopyranoside 4 and its alpha-anomer 34. Reduction of 4 with sodium borohydride-nickel chloride gave the 3-amino derivative 36, which was converted into the acetamido compound 38. Compounds 3, 3, and 36 possess high oral antithrombotic activity, which decreases on acetylation of the amino group in 38. The alpha-anomer 34 was inactive. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00079-7