Succinic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-benzyloxy-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester | 173725-91-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: Succinic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-benzyloxy-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester
• 英文别名: 1-O-[(2R,3S,4S,5R,6S)-5-benzoyloxy-4-hydroxy-6-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] 4-O-[(2R,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl] butanedioate
• CAS: 173725-91-2
• 化学式: C₆₄H₆₄O₁₄S
• 分子量: 1089.27
• InChiKey: XBASLMOSWWZHNM-ZFRXECJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  79
• 可旋转键数：
  29
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Succinic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-benzyloxy-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以72%的产率得到Benzoic acid (1S,5R,6R,7S,8S,15R,16R,18S,19R)-6,7,18-tris-benzyloxy-5,16-bis-benzyloxymethyl-10,13-dioxo-2,4,9,14,17-pentaoxa-tricyclo[13.4.0.0^3,8]nonadec-19-yl ester
  参考文献：
  名称：

  Anomeric selectivity during intramolecular mannosylation of succinyl bridged glycosides 1

  摘要：

  Alkyl and phenyl 1-thio-D-mannosides linked by a succinyl bridge via 2-O and 6-O, respectively to various positions of a D-glucoside are cyclised with N-iodosuccinimide to give the corresponding alpha- and beta-linked disaccharides depending on the connected positions.

  DOI：

  10.1016/0040-4039(95)01952-e
• 作为产物：
  描述：

  phenyl 3,4,6-tri-O-benzyl-2-O-(3-carboxypropanoyl)-1-thio-α-D-mannopyranoside 在 硫脲 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 Succinic acid (2R,3S,4S,5R,6S)-5-benzoyloxy-6-benzyloxy-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Anomeric selectivity during intramolecular mannosylation of succinyl bridged glycosides 1

  摘要：

  Alkyl and phenyl 1-thio-D-mannosides linked by a succinyl bridge via 2-O and 6-O, respectively to various positions of a D-glucoside are cyclised with N-iodosuccinimide to give the corresponding alpha- and beta-linked disaccharides depending on the connected positions.

  DOI：

  10.1016/0040-4039(95)01952-e

文献信息

• Anomeric selectivity during intramolecular mannosylation of succinyl bridged glycosides 1
  作者：Thomas Ziegler、Gregor Lemanski、Albert Rakoczy

  DOI：10.1016/0040-4039(95)01952-e

  日期：1995.12

  Alkyl and phenyl 1-thio-D-mannosides linked by a succinyl bridge via 2-O and 6-O, respectively to various positions of a D-glucoside are cyclised with N-iodosuccinimide to give the corresponding alpha- and beta-linked disaccharides depending on the connected positions.