[(2R,3R,4S,5S,6R)-5-acetyloxy-6-ethylsulfanyl-3,4-bis(phenylmethoxy)oxan-2-yl]methyl acetate | 138566-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5S,6R)-5-acetyloxy-6-ethylsulfanyl-3,4-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 138566-31-1
• 化学式: C₂₆H₃₂O₇S
• 分子量: 488.602
• InChiKey: ILSVWULNFFXYDR-PUHDZGQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6R)-5-acetyloxy-6-ethylsulfanyl-3,4-bis(phenylmethoxy)oxan-2-yl]methyl acetate 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 (2R,3S,4R,5R,6R)-6-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-[(2S,3S,4S,5R,6R)-2-methoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)oxan-3-ol
  参考文献：
  名称：

  Synthesis of a peptidyldimannosyl phosphate: fragment of the variant-specific surface glycoprotein membrane anchor from trypanosoma brucei

  摘要：

  Condensation of protected beta-benzyl-aspartate 4 with 2-amino-ethanol, subsequent deprotection of the amino function and coupling with N',N'-di-benzylocarbonyl-lysine (7) afforded the peptidyl alcohol 8. Glycosylation of methyl 3,4,6 tri-O-benzyl-alpha-D-mannopyranoside (11) by ethyl 2,6-di-O-benzoyl-3,4-di-O-benzyl-1-thio-alpha-D-mannopyranoside (14) gave, after debenzoylation and protection of the 2'-hydroxyl function, the suitably protected dimannoside 21. Phosphitylation of 21 with benzyloxy-bis-(N, N-diisopropylamino)phosphine (18) followed by the addition of 8 gave, after oxidation and subsequent hydrogenolysis of the benzyl groups, the title compound in a good yield.

  DOI：

  10.1016/0040-4039(91)80242-x
• 作为产物：
  描述：

  3,4,6-三-O-苄基-beta-D-吡喃甘露糖-1,2-(甲基原乙酸酯) 在 三氟甲磺酸三甲基硅酯 、 硫酸 作用下， 以 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 生成 [(2R,3R,4S,5S,6R)-5-acetyloxy-6-ethylsulfanyl-3,4-bis(phenylmethoxy)oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of a peptidyldimannosyl phosphate: fragment of the variant-specific surface glycoprotein membrane anchor from trypanosoma brucei

  摘要：

  Condensation of protected beta-benzyl-aspartate 4 with 2-amino-ethanol, subsequent deprotection of the amino function and coupling with N',N'-di-benzylocarbonyl-lysine (7) afforded the peptidyl alcohol 8. Glycosylation of methyl 3,4,6 tri-O-benzyl-alpha-D-mannopyranoside (11) by ethyl 2,6-di-O-benzoyl-3,4-di-O-benzyl-1-thio-alpha-D-mannopyranoside (14) gave, after debenzoylation and protection of the 2'-hydroxyl function, the suitably protected dimannoside 21. Phosphitylation of 21 with benzyloxy-bis-(N, N-diisopropylamino)phosphine (18) followed by the addition of 8 gave, after oxidation and subsequent hydrogenolysis of the benzyl groups, the title compound in a good yield.

  DOI：

  10.1016/0040-4039(91)80242-x