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 | 150843-10-0

• 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: 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
• CAS: 150843-10-0
• 化学式: C₃₈H₄₆O₁₁
• 分子量: 678.777
• InChiKey: DJRWHIVYRZLFNI-VVYVWSPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  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 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到(4R,5R,6R)-4,5-bis(benzyloxy)-2-(((4R,5R,6R)-5-(benzyloxy)-2-carboxy-2-methoxy-6-methyltetrahydro-2H-pyran-4-yl)oxy)-6-methyltetrahydro-2H-pyran-2-carboxylic acid
  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：

  (4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester 在 4 A molecular sieve 、 camphor-10-sulfonic acid 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 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

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.