(4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester | 150843-09-7

• 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,5R,6R)-4,5-Bis-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (4R,5R,6R)-6-methyl-4,5-bis(phenylmethoxy)-2-phenylsulfanyloxane-2-carboxylate
• CAS: 150843-09-7
• 化学式: C₂₈H₃₀O₅S
• 分子量: 478.609
• InChiKey: AKENJOJOHZZHED-FSZHJMDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5S,6R)-5-Benzyloxy-4-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester 、 (4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以20%的产率得到methyl (4R,5R,6R)-2-[(4R,5R,6R)-2-methoxy-2-methoxycarbonyl-6-methyl-5-phenylmethoxyoxan-4-yl]oxy-6-methyl-4,5-bis(phenylmethoxy)oxane-2-carboxylate
  参考文献：
  名称：

  Sequential diastereoselective free radical reactions: Synthesis of an advanced olivomycin A C–D disaccharide

  摘要：

  The synthesis of an advanced olivomycin A C-D disaccharide is described in which the anomeric configuration of both 2-deoxy-beta-glycosidic linkages is determined by a sequential diastereoselective radical reaction at the end of the synthesis.

  DOI：

  10.1016/s0040-4039(00)79162-3
• 作为产物：
  描述：

  3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-D-glucal 在 吡啶 、 盐酸 、 甲醇 、 氟化铵 、 三正丁基氢锡 、 magnesium monoperoxyphthalate hexahydrate 、 N,N-二异丙基乙胺 、 naphthalen-1-yl-lithium 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 丁酮 为溶剂， 生成 (4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Sequential diastereoselective free radical reactions: Synthesis of an advanced olivomycin A C–D disaccharide

  摘要：

  The synthesis of an advanced olivomycin A C-D disaccharide is described in which the anomeric configuration of both 2-deoxy-beta-glycosidic linkages is determined by a sequential diastereoselective radical reaction at the end of the synthesis.

  DOI：

  10.1016/s0040-4039(00)79162-3

文献信息

• Sequential diastereoselective free radical reactions: Synthesis of an advanced olivomycin A C–D disaccharide
  作者：David Crich、Frank Hermann

  DOI：10.1016/s0040-4039(00)79162-3

  日期：1993.5

  The synthesis of an advanced olivomycin A C-D disaccharide is described in which the anomeric configuration of both 2-deoxy-beta-glycosidic linkages is determined by a sequential diastereoselective radical reaction at the end of the synthesis.