Acetic acid (2S,3S,4R,6R)-6-acetoxy-4-acetylsulfanyl-2-methyl-tetrahydro-pyran-3-yl ester | 136505-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Acetic acid (2S,3S,4R,6R)-6-acetoxy-4-acetylsulfanyl-2-methyl-tetrahydro-pyran-3-yl ester
• 英文别名: Acetic acid (2S,3S,4R,6S)-6-acetoxy-4-acetylsulfanyl-2-methyl-tetrahydro-pyran-3-yl ester；Acetic acid (2S,3S,4S,6R)-6-acetoxy-4-acetylsulfanyl-2-methyl-tetrahydro-pyran-3-yl ester；Acetic acid (2S,3S,4S,6S)-6-acetoxy-4-acetylsulfanyl-2-methyl-tetrahydro-pyran-3-yl ester；1,4-Di-O-acetyl-3-S-acetyl-3,6-dideoxy-L-lyxo/xylo-hexopyranose
• CAS: 136505-49-2；136598-48-6；136598-49-7；136598-50-0；136598-51-1
• 化学式: C₁₂H₁₈O₆S
• 分子量: 290.337
• InChiKey: PJUDEAFGXQOJQC-STHGTBNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4R,6R)-6-acetoxy-4-acetylsulfanyl-2-methyl-tetrahydro-pyran-3-yl ester 在 盐酸 、 3 A molecular sieve 、 silica gel 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 二氯甲烷 、 xylene 、 苯 为溶剂， 反应 1.0h， 生成 7-O-(4-O-Acetyl-3-S-acetyl-3-thio-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)-14-O-tert-butyldimethylsilyl-adriamycinone
  参考文献：
  名称：

  A facile method for preparation of 3-thio-sugars and 3-thio-glycals. synthesis of 3′-mercapto-3′-deamino-doxorubicin

  摘要：

  General method for the preparation of synthetically useful 3-thio-glycals and biologically important 3-thio-sugars is described. The 3-thio-2,3,6-trideoxy-L-hexopyranoses (13,14) and corresponding 3-S-acetyl-1,5-anhydro-3-thio-L-hex-1-enitols (15-18) were synthesized using 3,4-di-O-acetyl-L-fucal (1) and 3,4-di-O-acetyl-L-rhamnal (2) as substrates. The 3-thio-glycals were successfully employed for the synthesis of 3'-mercapto-3'-deamino-doxorubicin and its analogues.

  DOI：

  10.1016/s0040-4039(00)92694-7
• 作为产物：
  描述：

  2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 在 吡啶 、 水 作用下， 以 水 为溶剂， 反应 12.0h， 生成 Acetic acid (2S,3S,4R,6R)-6-acetoxy-4-acetylsulfanyl-2-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  A facile method for preparation of 3-thio-sugars and 3-thio-glycals. synthesis of 3′-mercapto-3′-deamino-doxorubicin

  摘要：

  General method for the preparation of synthetically useful 3-thio-glycals and biologically important 3-thio-sugars is described. The 3-thio-2,3,6-trideoxy-L-hexopyranoses (13,14) and corresponding 3-S-acetyl-1,5-anhydro-3-thio-L-hex-1-enitols (15-18) were synthesized using 3,4-di-O-acetyl-L-fucal (1) and 3,4-di-O-acetyl-L-rhamnal (2) as substrates. The 3-thio-glycals were successfully employed for the synthesis of 3'-mercapto-3'-deamino-doxorubicin and its analogues.

  DOI：

  10.1016/s0040-4039(00)92694-7