thexyldimethylsilyl 3-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-2-O-benzoyl-4,6-O-benzylidene-3-thio-β-D-galactopyranoside | 297730-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: thexyldimethylsilyl 3-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-2-O-benzoyl-4,6-O-benzylidene-3-thio-β-D-galactopyranoside
• 英文别名: [(2S,4aR,6S,7S,8S,8aS)-8-[[(5S,6R,7S,8R,8aR)-6,7,8-triacetyloxy-3-oxo-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-5-yl]sulfanyl]-6-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• CAS: 297730-85-9
• 化学式: C₄₁H₅₃NO₁₄SSi
• 分子量: 844.022
• InChiKey: QWCHLFYVRHQTPN-RQCHTWSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  58.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  171.66
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  thexyldimethylsilyl 3-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-2-O-benzoyl-4,6-O-benzylidene-3-thio-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到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
• 作为产物：
  描述：

  (1R)-1,2,3,4-tetra-O-acetyl-5N,6O-oxomethylidenenojirimycin 在 三氟甲磺酸三甲基硅酯 、 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 thexyldimethylsilyl 3-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-2-O-benzoyl-4,6-O-benzylidene-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