methyl (5R,10R,13R)-labda-8-en-15-oate | 152269-96-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (5R,10R,13R)-labda-8-en-15-oate
• 英文别名: enantio-Labd-8-en-15-saeure-methylester；methyl (3R)-5-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoate
• CAS: 152269-96-0
• 化学式: C₂₁H₃₆O₂
• 分子量: 320.516
• InChiKey: YGWNSYBZXZHSJI-FPDPHYFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2'-acetoxyglyceryl (5R,10R,13R)-labd-8-en-15-oate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 methyl (5R,10R,13R)-labda-8-en-15-oate
  参考文献：
  名称：

  New diterpenoic acid glycerides from the antarctic nudibranch austrodoris kerguelensis

  摘要：

  A single specimen of the Antarctic nudibranch Austrodoris kerguelensis contained two major glyceride esters, 2'-acetoxyglyceryl (5R,10R,13R)-labda-8-en-15-oate (1) and 3'-acetoxyglyceryl (5R,10R,13R)-labda-8-en-15-oate (4), the diketones 6 and 7 that arise from oxidation of the 8,9-olefinic bond, and glyceryl (5R,10R,13R)-7-ketolabda-8-en-15-oate (8). The probable source of these metabolites is discussed.

  DOI：

  10.1016/s0040-4020(01)80714-6

文献信息

• Chemoenzymatic Synthesis of (+)-.ALPHA.-Polypodatetraene and Methyl (5R,10R,13R)-Labda-8-en-15-oate
  作者：Masako Kinoshita、Takahiro Miyake、Yuusuke Arima、Minako Oguma、Hiroyuki Akita

  DOI：10.1248/cpb.56.118

  日期：——

  The reported enzymatic resolution products acetate of (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal} (8aS)-5 (>99% ee)] and [(1R,4aR,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-oxo-trans-naphthalene-1-methanol-2-ethylene acetal (8aR)-4 (98% ee) were converted to (+)-α-polypodatetraene (1) and methyl (5R,10R,13R)-labda-8-en-15-oate (2), respectively. For the synthesis of (5R,10R,13R)-2, chiral isoprene congener (3S)-26 corresponding to the right part of 2 was synthesized based on the lipase-assisted resolution of (±)-2-methyl-3- (p-methoxyphenyl)propanol (17).

  已报道的酶解产物(1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-十氢-5,5,8a-三甲基-2-氧代-反式-萘-1-甲醇-2-乙烯缩醛的乙酸酯} (8aS)-5 (>99% ee)]和[(1R,4aR,8aR)-1,2,3,4、4a,5,6,7,8,8a-十氢-5,5,8a-三甲基-2-氧代-反式-萘-1-甲醇-2-乙烯缩醛 (8aR)-4 (98% ee)]分别转化为 (+)-α-polypodatetraene (1) 和 (5R,10R,13R)-labda-8-烯-15-酸甲酯 (2)。为了合成 (5R,10R,13R)-2，根据脂肪酶辅助解析 (±)-2- 甲基-3-（对甲氧基苯基）丙醇 (17) 的方法，合成了对应于 2 右半部分的手性异戊二烯同系物 (3S)-26。
• New diterpenoic acid glycerides from the antarctic nudibranch austrodoris kerguelensis
  作者：Michael T. Davies-Coleman、D.John Faulkner

  DOI：10.1016/s0040-4020(01)80714-6

  日期：1991.12

  A single specimen of the Antarctic nudibranch Austrodoris kerguelensis contained two major glyceride esters, 2'-acetoxyglyceryl (5R,10R,13R)-labda-8-en-15-oate (1) and 3'-acetoxyglyceryl (5R,10R,13R)-labda-8-en-15-oate (4), the diketones 6 and 7 that arise from oxidation of the 8,9-olefinic bond, and glyceryl (5R,10R,13R)-7-ketolabda-8-en-15-oate (8). The probable source of these metabolites is discussed.