2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-α-D-glucopyranosyl trichloroacetimidate | 297730-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: 1-O-trichloroacetimidate-2,3,4-tri-O-acetyl-5N,6O-oxomethylidenenojirimycin；[(5R,6R,7S,8R,8aR)-6,7-diacetyloxy-3-oxo-5-(2,2,2-trichloroethanimidoyl)oxy-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-8-yl] acetate
• CAS: 297730-79-1
• 化学式: C₁₅H₁₇Cl₃N₂O₉
• 分子量: 475.667
• InChiKey: JWCCBBNGXHTCEI-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 N-phenylmethoxycarbonyl-S-(6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester
  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 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 8.0h， 生成 2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-α-D-glucopyranosyl trichloroacetimidate
  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