Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester | 201139-14-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3R,4S,5R,6R)-5-hydroxy-2-[(E,2S,3R)-2-(octadecanoylamino)-3-phenylmethoxyoctadec-4-enoxy]-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 201139-14-2
• 化学式: C₇₀H₁₀₃NO₉
• 分子量: 1102.59
• InChiKey: CETVIBMVHNKJFV-QGWQKSKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.1
• 重原子数：
  80
• 可旋转键数：
  47
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester 、 C₆₅H₆₉N₂O₁₅P 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到
  参考文献：
  名称：

  “Armed-disarmed” glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide

  摘要：

  A stereocontrolled synthesis of globotriaosylcernmide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting "armed-disarmed" glycosidation methodology bared on glycosyl donors and accepters carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl-(1-->4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10365-3
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-5-(2-chloroacetyl)oxy-2-[(E,2S,3R)-2-(octadecanoylamino)-3-phenylmethoxyoctadec-4-enoxy]-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] benzoate 在 2,6-二甲基吡啶 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以98%的产率得到Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  基于带有含磷离去基团的糖基供体和受体的化学选择性糖苷化策略：神经节苷脂GM 3的聚合合成

  摘要：

  通过利用三个不同的含磷离去基团，实现神经节苷脂GM 3的聚合合成，其中关键特征包括在三氟甲磺酸和三氟甲基磺酸的帮助下，将唾液酸亚磷酸酯的化学和区域选择性α-糖基化与部分苄基化的半乳糖基四甲基磷酸二氨基甲酸酯。 α-唾液酸基-（2→3）-半乳糖基供体与葡糖基神经酰胺结构单元的传统上不常见的偶联，该结构单元具有通过磷酸二苯酯方法预先构建在葡萄糖中的β- O-连接的神经酰胺。

  DOI：

  10.1016/s0040-4039(00)01343-5

文献信息

• “Armed-disarmed” glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide
  作者：Shun-ichi Hashimoto、Hiroki Sakamoto、Takeshi Honda、Hiroshi Abe、Sei-ichi Nakamura、Shiro Ikegami

  DOI：10.1016/s0040-4039(97)10365-3

  日期：1997.12

  A stereocontrolled synthesis of globotriaosylcernmide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting "armed-disarmed" glycosidation methodology bared on glycosyl donors and accepters carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl-(1-->4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient. (C) 1997 Elsevier Science Ltd.
• Chemoselective glycosidation strategy based on glycosyl donors and acceptors carrying phosphorus-containing leaving groups: a convergent synthesis of ganglioside GM3
  作者：Hiroki Sakamoto、Seiichi Nakamura、Toshifumi Tsuda、Shunichi Hashimoto

  DOI：10.1016/s0040-4039(00)01343-5

  日期：2000.9

  A convergent synthesis of ganglioside GM3 has been achieved by capitalizing on three different phosphorus-containing leaving groups, in which the key features involve a chemo- and regioselective α-glycosidation of sialyl phosphite with partially benzylated galactosyl tetramethylphosphorodiamidate by the aid of trifluoromethanesulfonic acid and a traditionally uncommon coupling of an α-sialyl-(2→3)-galactosyl

  通过利用三个不同的含磷离去基团，实现神经节苷脂GM 3的聚合合成，其中关键特征包括在三氟甲磺酸和三氟甲基磺酸的帮助下，将唾液酸亚磷酸酯的化学和区域选择性α-糖基化与部分苄基化的半乳糖基四甲基磷酸二氨基甲酸酯。 α-唾液酸基-（2→3）-半乳糖基供体与葡糖基神经酰胺结构单元的传统上不常见的偶联，该结构单元具有通过磷酸二苯酯方法预先构建在葡萄糖中的β- O-连接的神经酰胺。