(4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal | 152732-87-1

• 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: (4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal
• 英文别名: [(2R)-2-[(1S)-2-[(4-bromophenyl)methoxy]-1-[tert-butyl(dimethyl)silyl]oxyethyl]-5-oxopentyl] benzoate
• CAS: 152732-87-1
• 化学式: C₂₇H₃₇BrO₅Si
• 分子量: 549.577
• InChiKey: FTHMTOYBIREYGB-ILBGXUMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal 在 palladium on activated charcoal 吡啶 、 盐酸 、 硫酸氢铵 、 三甲基氯硅烷 、 叔丁基二甲硅基三氟甲磺酸酯 、 氢气 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 25.0 ℃ 、506.62 kPa 条件下， 反应 28.67h， 生成 1-(2,3,4-trideoxy-4-C-benzoyloxymethyl-6-O-benzoyl-β-D-erythro-hexopyranosyl)uracil
  参考文献：
  名称：

  Synthesis of 4-C-hydroxymethyl hexopyranosyl nucleosides as potential inhibitors of HIV

  摘要：

  The synthesis of 1-(2,3,4-trideoxy-4-C-hydroxymethyl-beta-D-erythro-hexopyranosyl)thymine (13), -uracil (15), -cytosine (16) and 9-(2,3,4-trideoxy-4-C-hydroxymethyl-beta-D-erythro-hexopyranosyl)adenine (18) are described. The nucleoside analogues were evaluated for their anti-HIV activity in vitro.

  DOI：

  10.1016/s0040-4020(01)96269-6
• 作为产物：
  描述：

  (2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(2-propenyl)-1,2,4-butanetriol 在 重铬酸吡啶 、 sodium perborate 、 dimethyl sulfide borane 、 乙酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal
  参考文献：
  名称：

  Synthesis of 4-C-hydroxymethyl hexopyranosyl nucleosides as potential inhibitors of HIV

  摘要：

  The synthesis of 1-(2,3,4-trideoxy-4-C-hydroxymethyl-beta-D-erythro-hexopyranosyl)thymine (13), -uracil (15), -cytosine (16) and 9-(2,3,4-trideoxy-4-C-hydroxymethyl-beta-D-erythro-hexopyranosyl)adenine (18) are described. The nucleoside analogues were evaluated for their anti-HIV activity in vitro.

  DOI：

  10.1016/s0040-4020(01)96269-6

文献信息

• Synthesis of 4-C-hydroxymethyl hexopyranosyl nucleosides as potential inhibitors of HIV
  作者：Magnus Björsne、Björn Classon、ngemar Kvarnström、Bertil Samuelsson

  DOI：10.1016/s0040-4020(01)96269-6

  日期：1993.9

  The synthesis of 1-(2,3,4-trideoxy-4-C-hydroxymethyl-beta-D-erythro-hexopyranosyl)thymine (13), -uracil (15), -cytosine (16) and 9-(2,3,4-trideoxy-4-C-hydroxymethyl-beta-D-erythro-hexopyranosyl)adenine (18) are described. The nucleoside analogues were evaluated for their anti-HIV activity in vitro.