(2R,3R,4R,4aS,7S,8aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-hexahydro-pyrano[3,2-b]pyridin-6-one | 918416-01-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,4aS,7S,8aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-hexahydro-pyrano[3,2-b]pyridin-6-one
• 英文别名: (2R,3R,4R,4aS,7S,8aS)-7-hydroxy-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-2,3,4,4a,5,7,8,8a-octahydropyrano[3,2-b]pyridin-6-one
• CAS: 918416-01-0
• 化学式: C₃₀H₃₃NO₆
• 分子量: 503.595
• InChiKey: ZEFNDUJILUTKTB-RXQXDSFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,4aS,7S,8aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-hexahydro-pyrano[3,2-b]pyridin-6-one 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 22.0h， 生成 Acetic acid (2R,3R,4R,4aS,7S,8aS)-3,7-diacetoxy-2-acetoxymethyl-6-oxo-octahydro-pyrano[3,2-b]pyridin-4-yl ester
  参考文献：
  名称：

  Hybrid sugars as glycosidase inhibitors en route to 2-deoxy-2-amino C-glycosyl amino acids

  摘要：

  Sugar-azasugar hybrid molecules made up Of D-galactose with nojirimycin-delta-lactam and pyrrolidine analogues are synthesized using intramolecular cyclization as a key step from 2-nitro galactal and found to be glycosidase inhibitors. Further, some of the intermediate compounds are converted into 2-deoxy-2-amino C-glycosyl glycines and C-glycosyl alanines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.024
• 作为产物：
  描述：

  (2S,3S,4R,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-3-nitro-tetrahydro-pyran 在 盐酸 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 四氧化锇 、 碳酸氢钠 、 N-甲基吗啉氧化物 、 三乙胺 、 potassium bromide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 水 、 碳酸氢钠 、 溶剂黄146 、 丙酮 、 叔丁醇 为溶剂， 反应 44.5h， 生成 (2R,3R,4R,4aS,7S,8aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-hexahydro-pyrano[3,2-b]pyridin-6-one
  参考文献：
  名称：

  Hybrid sugars as glycosidase inhibitors en route to 2-deoxy-2-amino C-glycosyl amino acids

  摘要：

  Sugar-azasugar hybrid molecules made up Of D-galactose with nojirimycin-delta-lactam and pyrrolidine analogues are synthesized using intramolecular cyclization as a key step from 2-nitro galactal and found to be glycosidase inhibitors. Further, some of the intermediate compounds are converted into 2-deoxy-2-amino C-glycosyl glycines and C-glycosyl alanines. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.024

文献信息

• Hybrid sugars as glycosidase inhibitors en route to 2-deoxy-2-amino C-glycosyl amino acids
  作者：K. Jayakanthan、Yashwant D. Vankar

  DOI：10.1016/j.tetlet.2006.10.024

  日期：2006.12

  Sugar-azasugar hybrid molecules made up Of D-galactose with nojirimycin-delta-lactam and pyrrolidine analogues are synthesized using intramolecular cyclization as a key step from 2-nitro galactal and found to be glycosidase inhibitors. Further, some of the intermediate compounds are converted into 2-deoxy-2-amino C-glycosyl glycines and C-glycosyl alanines. (c) 2006 Elsevier Ltd. All rights reserved.