Thioacetic acid S-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-hydroxy-tetrahydro-pyran-2-ylmethyl) ester | 291297-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Thioacetic acid S-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-hydroxy-tetrahydro-pyran-2-ylmethyl) ester
• CAS: 291297-63-7
• 化学式: C₂₉H₃₂O₆S
• 分子量: 508.635
• InChiKey: QTNHEAGKLODRJK-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  三氯乙腈 、 Thioacetic acid S-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-hydroxy-tetrahydro-pyran-2-ylmethyl) ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 以70%的产率得到Thioacetic acid S-[(2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethyl] ester
  参考文献：
  名称：

  Structural determination of sulfoquinovosyldiacylglycerol by chiral syntheses

  摘要：

  Chiral sulfoquinovosyldiacylglycerols (SQDGs) have been synthesized to determine the absolute stereochemistry and the biological activities. The H-1 NMR spectrum of a natural SQDG is comparable to that of synthetic (2S)-SQDC rather than that of the (2R) analogue. The biological activity of the respective isomers for DNA polymerase alpha and beta inhibition was not distinguishable in the enzymatic assay. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00638-9
• 作为产物：
  描述：

  烯丙基-2,3,4-三-苄氧基-ALPHA-D-葡萄糖苷 在 4-二甲氨基吡啶 、 palladium dichloride 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 Thioacetic acid S-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-hydroxy-tetrahydro-pyran-2-ylmethyl) ester
  参考文献：
  名称：

  Structural determination of sulfoquinovosyldiacylglycerol by chiral syntheses

  摘要：

  Chiral sulfoquinovosyldiacylglycerols (SQDGs) have been synthesized to determine the absolute stereochemistry and the biological activities. The H-1 NMR spectrum of a natural SQDG is comparable to that of synthetic (2S)-SQDC rather than that of the (2R) analogue. The biological activity of the respective isomers for DNA polymerase alpha and beta inhibition was not distinguishable in the enzymatic assay. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00638-9