(2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-hexanoic acid | 869475-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-hexanoic acid
• 英文别名: (2R,3S,4R,5R)-5-[(4-methoxyphenyl)methoxy]-2,3,4,6-tetrakis(phenylmethoxy)hexanoic acid
• CAS: 869475-40-1
• 化学式: C₄₂H₄₄O₈
• 分子量: 676.807
• InChiKey: PENPCKGACXMOIB-PRURZLHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  50
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-hexanoic acid 在 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-hexanoyl chloride
  参考文献：
  名称：

  An amide orthoesterification route to N-(1′-alkylthioglucopyranosyl)indoles

  摘要：

  The addition of 3-methylindolylmagnesium bromide to tetra-O-benzyl-alpha-D-gluconothionolactone yields the expected indole N-gluconothioamide as its hemiorthothioamide tautomer. The thiol function is alkylated to yield the corresponding orthothioamide, a l'-alkylthio-substituted N-glycoside. Alternatively, the l'-alkylthio-N-glycoside can be accessed from the corresponding indole N-gluconamide via a boron trifluoride-etherate mediated orthoesterification with ethanethiol. Radical reduction of the orthothioamide yields the N-glycosides in 2:1 stereoselectivity in favor of the beta-N-glycoside, while reduction via the oxonium ion leads to an improved 6:1 selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.135
• 作为产物：
  描述：

  tert-Butyl-dimethyl-[(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-hexyloxy]-silane 在 四丁基氯化铵 、 碳酸氢钠 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 四丁基氟化铵 、 potassium bromide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-hexanoic acid
  参考文献：
  名称：

  An amide orthoesterification route to N-(1′-alkylthioglucopyranosyl)indoles

  摘要：

  The addition of 3-methylindolylmagnesium bromide to tetra-O-benzyl-alpha-D-gluconothionolactone yields the expected indole N-gluconothioamide as its hemiorthothioamide tautomer. The thiol function is alkylated to yield the corresponding orthothioamide, a l'-alkylthio-substituted N-glycoside. Alternatively, the l'-alkylthio-N-glycoside can be accessed from the corresponding indole N-gluconamide via a boron trifluoride-etherate mediated orthoesterification with ethanethiol. Radical reduction of the orthothioamide yields the N-glycosides in 2:1 stereoselectivity in favor of the beta-N-glycoside, while reduction via the oxonium ion leads to an improved 6:1 selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.135

文献信息

• An amide orthoesterification route to N-(1′-alkylthioglucopyranosyl)indoles
  作者：Tahar Belhadj、Peter G. Goekjian

  DOI：10.1016/j.tetlet.2005.09.135

  日期：2005.11

  The addition of 3-methylindolylmagnesium bromide to tetra-O-benzyl-alpha-D-gluconothionolactone yields the expected indole N-gluconothioamide as its hemiorthothioamide tautomer. The thiol function is alkylated to yield the corresponding orthothioamide, a l'-alkylthio-substituted N-glycoside. Alternatively, the l'-alkylthio-N-glycoside can be accessed from the corresponding indole N-gluconamide via a boron trifluoride-etherate mediated orthoesterification with ethanethiol. Radical reduction of the orthothioamide yields the N-glycosides in 2:1 stereoselectivity in favor of the beta-N-glycoside, while reduction via the oxonium ion leads to an improved 6:1 selectivity. (c) 2005 Elsevier Ltd. All rights reserved.