tert-Butyl-dimethyl-[(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-hexyloxy]-silane | 869475-43-4

• 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: tert-Butyl-dimethyl-[(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-hexyloxy]-silane
• CAS: 869475-43-4
• 化学式: C₄₈H₆₀O₇Si
• 分子量: 777.086
• InChiKey: UDUGMJOHKAMBDB-PXZLHRPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.58
• 重原子数：
  56.0
• 可旋转键数：
  23.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-甲氧基氯苄 、 (2R,3R,4R,5S)-6-[tert-butyl(dimethyl)silyl]oxy-1,3,4,5-tetrakis(phenylmethoxy)hexan-2-ol 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到tert-Butyl-dimethyl-[(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-hexyloxy]-silane
  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