(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol | 869475-37-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol
• 英文别名: (2S,3R,4S,5R,6R)-2-(3-methylindol-1-yl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane-2-thiol
• CAS: 869475-37-6
• 化学式: C₄₃H₄₃NO₅S
• 分子量: 685.884
• InChiKey: QNZUIZQGQFTAJI-MHUNNFNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol 、 碘甲烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到3-Methyl-1-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-2-yl)-1H-indole
  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：

  2,3,4,6-tetra-O-benzyl-1-thio-D-glucono-1,5-O-lactone 、 3-methylindolylmagnesium bromide 以 四氢呋喃 、 甲苯 为溶剂， 以32%的产率得到(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol
  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.