(2S,3R,4S,5R)-3,4,5-Triacetoxy-2-hexan-1-al | 157037-50-8

• 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: (2S,3R,4S,5R)-3,4,5-Triacetoxy-2-hexan-1-al
• 英文别名: [(2R,3S,4R,5R)-3,4-diacetyloxy-5-[benzhydryl(methyl)amino]-6-oxohexan-2-yl] acetate
• CAS: 157037-50-8
• 化学式: C₂₆H₃₁NO₇
• 分子量: 469.535
• InChiKey: GYTUVOSHVCGLLQ-LCBJMWRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R)-3,4,5-Triacetoxy-2-hexan-1-al 在 palladium on activated charcoal potassium cyanide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成 N-methyl-D-fucosamine
  参考文献：
  名称：

  An Enantioselective Synthesis of N-Methylfucosamine via Tandem C-C/C-O Bond Formation

  摘要：

  Optically pure D-(+)-N-methylfucosamine (8) has been synthesized from a TBDMS-protected methyl L-serinate benzophenone Schiff base (O'Donnell's Schiff base, 1) in seven steps in 13% overall yield. Efficient construction-of the requisite amino triol acetate 3a with the proper stereochemical configuration is accomplished in two steps with a chelation-controlled reduction-alkylation reaction using \Bu(2)AlH.Al-iBu(3)/E-LiCH=CHCH3, followed by oxidation with OsO4. Conversion of the Schiff base to the N-benzhydryl protecting group and methylation (Eschweiler-Clark) is accomplished in one pot with NaCNBH3 in ti;e presence of H2C=O. Deprotection and oxidation of the primary alcohol, followed by deacetylation with KCN, provided the desired product 8.

  DOI：

  10.1021/jo00095a039
• 作为产物：
  描述：

  (2S,3R,4S,5R)-3,4,5-Triacetoxy-2-hexan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (2S,3R,4S,5R)-3,4,5-Triacetoxy-2-hexan-1-al
  参考文献：
  名称：

  An Enantioselective Synthesis of N-Methylfucosamine via Tandem C-C/C-O Bond Formation

  摘要：

  Optically pure D-(+)-N-methylfucosamine (8) has been synthesized from a TBDMS-protected methyl L-serinate benzophenone Schiff base (O'Donnell's Schiff base, 1) in seven steps in 13% overall yield. Efficient construction-of the requisite amino triol acetate 3a with the proper stereochemical configuration is accomplished in two steps with a chelation-controlled reduction-alkylation reaction using \Bu(2)AlH.Al-iBu(3)/E-LiCH=CHCH3, followed by oxidation with OsO4. Conversion of the Schiff base to the N-benzhydryl protecting group and methylation (Eschweiler-Clark) is accomplished in one pot with NaCNBH3 in ti;e presence of H2C=O. Deprotection and oxidation of the primary alcohol, followed by deacetylation with KCN, provided the desired product 8.

  DOI：

  10.1021/jo00095a039