(Z)-Octadec-9-enoic acid (S)-2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester | 145014-07-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (Z)-Octadec-9-enoic acid (S)-2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester
• 英文别名: 1-O-oleoyl-3-O-beta-d-galactopyranosyl-sn-glycerol；[(2S)-2-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (Z)-octadec-9-enoate
• CAS: 145014-07-9
• 化学式: C₂₇H₅₀O₉
• 分子量: 518.689
• InChiKey: NFWYGIXMHGBINM-VRQQAJCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (9Z)-9-十八碳烯酸乙烯基酯 、 (Z)-Octadec-9-enoic acid (S)-2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester 在 Mucor jaranicus lipase (lipase M) 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以90%的产率得到(Z)-Octadec-9-enoic acid (2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[(S)-2-hydroxy-3-((Z)-octadec-9-enoyloxy)-propoxy]-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of 1-O-acyl-3-O-(6'-O-acyl-β-D-galactopyranosyl)-sn-glycerol

  摘要：

  Convenient synthesis of 1-O-acyl-3-O-(6'-O-acyl-beta-D-galactopyranosyl)-sn-glycerol was studied. The lipase from Achromobacter sp, catalyzed acylation of 3-O-beta-D-galactopyranosyl-sn-glycerol, which contains two primary hydroxyl functions, proceeded regioselectively to furnish 1-O-acyl-3-O-beta-D-galactopyranosyl-sn-glycerol.

  DOI：

  10.1016/0040-4020(95)00299-n
• 作为产物：
  描述：

  (9Z)-9-十八碳烯酸乙烯基酯 、 2,3-二羟基丙基吡喃己糖苷 以 吡啶 为溶剂， 反应 72.0h， 生成 (Z)-Octadec-9-enoic acid (S)-2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester 、
  参考文献：
  名称：

  Enzymatic Regioselective Acylation of 3-O-.BETA.-D-Galactopyranosyl-sn-glycerol by Achromobacter sp. Lipase.

  摘要：

  Achromobacter sp. 脂肪酶选择性地对3-O-β-D-半乳糖吡喃糖基-sn-甘油的两个主要羟基中的sn-1碳上的羟基进行了酰化。

  DOI：

  10.1248/cpb.42.751

文献信息

• Enzymatic Regioselective Acylation of 3-O-.BETA.-D-Galactopyranosyl-sn-glycerol by Achromobacter sp. Lipase.
  作者：Takashi MORIMOTO、Nobutoshi MURAKAMI、Akito NAGATSU、Jinsaku SAKAKIBARA

  DOI：10.1248/cpb.42.751

  日期：——

  Achromobacter sp. lipase regioselectively acylated the hydroxyl group on sn-1 carbon among the two primary hydroxyl groups of 3-O-β-D-galactopyranosyl-sn-glycerol.

  Achromobacter sp. 脂肪酶选择性地对3-O-β-D-半乳糖吡喃糖基-sn-甘油的两个主要羟基中的sn-1碳上的羟基进行了酰化。
• Chemoenzymatic synthesis of 1-O-acyl-3-O-(6'-O-acyl-β-D-galactopyranosyl)-sn-glycerol
  作者：Takashi Morimoto、Akito Nagatsu、Nobutoshi Murakami、Jinsaku Sakakibara

  DOI：10.1016/0040-4020(95)00299-n

  日期：1995.6

  Convenient synthesis of 1-O-acyl-3-O-(6'-O-acyl-beta-D-galactopyranosyl)-sn-glycerol was studied. The lipase from Achromobacter sp, catalyzed acylation of 3-O-beta-D-galactopyranosyl-sn-glycerol, which contains two primary hydroxyl functions, proceeded regioselectively to furnish 1-O-acyl-3-O-beta-D-galactopyranosyl-sn-glycerol.