thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside | 297730-86-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside
• CAS: 297730-86-0
• 化学式: C₃₅H₄₇NO₁₁SSi
• 分子量: 717.91
• InChiKey: NYCOUGBOQVBHFX-RANDFOJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  49.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  153.45
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside 在 对甲苯磺酸 、 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到thexyldimethylsilyl 2-O-benzoyl-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside
  参考文献：
  名称：

  5-Amino-5-Deoxy-1-Thioglucopyranosides-Synthesis of Thioglycoside Derivatives of Nojirimycin

  摘要：

  N-Benzyloxycarbonyl-protected 5-amino-5-deoxyglucofuranose derivative 1 could be readily transformed into 6-O, N-carbonylidene nojirimycin 3 which afforded the corresponding piperidinosyl trichloroacetimidate 6. This compound turned out to be a versatile piperidinosyl donor. Reaction with various mercaptans as accepters in the presence of TMSOTf as catalyst gave 5-aza-1-thioglucopyranosides 7a-c, 9, and 13 which were successfully deprotected.

  DOI：

  10.1080/07328300008544110
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-α-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-3-thio-β-D-galactopyranoside
  参考文献：
  名称：

  5-Amino-5-Deoxy-1-Thioglucopyranosides-Synthesis of Thioglycoside Derivatives of Nojirimycin

  摘要：

  N-Benzyloxycarbonyl-protected 5-amino-5-deoxyglucofuranose derivative 1 could be readily transformed into 6-O, N-carbonylidene nojirimycin 3 which afforded the corresponding piperidinosyl trichloroacetimidate 6. This compound turned out to be a versatile piperidinosyl donor. Reaction with various mercaptans as accepters in the presence of TMSOTf as catalyst gave 5-aza-1-thioglucopyranosides 7a-c, 9, and 13 which were successfully deprotected.

  DOI：

  10.1080/07328300008544110