(2S,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-ethoxythiocarbonylsulfanyl-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 139534-83-1

• 英文名称: (2S,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-ethoxythiocarbonylsulfanyl-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,4S,5R,6S)-5-acetamido-4-benzoyloxy-2-ethoxycarbothioylsulfanyl-6-[(1S,2R)-1,2,3-tribenzoyloxypropyl]oxane-2-carboxylate
• CAS: 139534-83-1
• 化学式: C₄₃H₄₁NO₁₃S₂
• 分子量: 843.929
• InChiKey: YESQJQKRQIQBLV-GGIGCTKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  59.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  179.06
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  Benzyl 4,6-O-benzylidene-β-D-galactopyranoside 、 (2S,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-ethoxythiocarbonylsulfanyl-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 甲基硫基溴化物 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 二异丙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以17%的产率得到(4S,5R,6S)-5-Acetylamino-4-benzoyloxy-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Glycosylation with sialic acid at HO-3 of three different O-protected D-galactosides in acetonitrile/dichloromethane at low temperature

  摘要：

  Three different O-protected D-galactosides have been compared as acceptors in alpha-sialoside synthesis using glycosyl donor 1, methylsulfenyl triflate as promoter, and acetonitrile/dichloromethane as solvent at - 70-degrees-C. The 6-O-benzylated acceptor 2 was the most efficient, the alpha(2-3) sialoside 5 was obtained in 39% isolated yield.

  DOI：

  10.1016/0040-4039(91)80133-q
• 作为产物：
  描述：

  (2R,4S,5R,6S)-5-Acetylamino-2,4-bis-benzoyloxy-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 氢溴酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 生成 (2S,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-ethoxythiocarbonylsulfanyl-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  α-selectivity and glycal formation are temperature dependent in glycosylation with sialic acid. Synthesis of a Neu5Acα(2-6)Gal thioglycoside building block

  摘要：

  The glycosylation with the N-acetylneuraminic acid (Neu5Ac) donor 1 of the 6-OH position of D-galactose in various nitriles promoted by methylsulfenyl triflate at different temperatures is reported. The proportion of alpha-sialoside increased and glycal 5 decreased at lower temperatures. A short route to a Neu5Ac-alpha(2-6)Gal thioglycoside building block is also described.

  DOI：

  10.1016/0040-4039(91)80132-p