ethyl 3-hydroxy-15-methylhexadecanoate | 214278-03-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-hydroxy-15-methylhexadecanoate
• CAS: 214278-03-2
• 化学式: C₁₉H₃₈O₃
• 分子量: 314.509
• InChiKey: DCDICQDUOBABJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxy-15-methylhexadecanoate 在 咪唑 、 4-二甲氨基吡啶 、 lithium hydroxide 、 ammonium hydroxide 、 四丁基氟化铵 、 双氧水 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R,3'R)-3-hydroxy-2-(3'-hydroxy-15'-methylhexadecanoylamino)-15-methyl-hexadecan-1-sulfonic acid
  参考文献：
  名称：

  合成的硫代霉素A和B，新的脂脂分离自Chryseobacterium sp.。

  摘要：

  硫杆菌素A（1）和B（2），新的磺脂从金黄葡萄菌中分离。von Willebrand因子拮抗剂，是从l-半胱氨酸开始立体选择性合成的。

  DOI：

  10.1016/s0040-4039(98)01456-7
• 作为产物：
  描述：

  magnesium,2-methylbutane,bromide 在 dilithium tetrachlorocuprate 、 4 A molecular sieve 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.67h， 生成 ethyl 3-hydroxy-15-methylhexadecanoate
  参考文献：
  名称：

  Synthesis of sphingosine relatives. Part 22. Synthesis of sulfobacin A, B and flavocristamide A, new sulfonolipids isolated from Chryseobacterium sp.

  摘要：

  硫宝卡辛A（1）、B（2）以及黄晶酰胺A（3），是从黄杆菌属中分离得到的新型磺酸脂类化合物，它们通过以L-半胱氨酸为起始原料进行了立体选择性合成。

  DOI：

  10.1039/a904258j

文献信息

• Optically active ceramides and process for producing the same
  申请人：Takasago International Corporation

  公开号：EP0856510B1

  公开（公告）日：2002-12-11
• Structural verification via convergent total synthesis of dipeptide–lipids isolated from Porphyromonas gingivalis
  作者：Christopher Dietz、Theresa K. Hart、Reza Nemati、Xudong Yao、Frank C. Nichols、Michael B. Smith

  DOI：10.1016/j.tet.2016.10.010

  日期：2016.11

  A periodontal pathogen, Porphyromonas gingivalis, produces two serine dipeptide lipid classes that we labeled lipid 654 and lipid 430, and both contain L-serine as the terminal amino acid. The lipid 654 and lipid 430 classes are each comprised of three species with differing fatty acid substitutions, but the most abundant species demonstrate unit masses of either 654 or 430, respectively. Recently we observed that the lipid 654 can be hydrolyzed by specific lipases to lipid 430. However, a substantial percentage of the naturally occurring lipid 654 cannot be enzymatically hydrolyzed to lipid 430. The observed partial hydrolysis could be due to the presence of a mixture of stereoisomers. Testing this theory requires structural verification of our so-called 654 and 430 by total synthesis. We present herein details of the convergent synthesis of lipids 430 and 654, which confirm the proposed structure of P. gingivalis lipid 654 to be (3R and 3S)-L-serine-2. The bis(fatty acid) (3R)-L-serine-2 was prepared as well as the synthetic precursor, serine dipeptide mono-fatty acid (3R)-L-serine-1, which is the structure of lipid 430. We also synthesized the (3S)-L-serine-2 diastereomer as well as (3S)-L-serine-1. Using these synthetic standards, we confirmed that PLA2-mediated hydrolysis of lipid 654 is enantioselective in that only the (3R)-L-serine-2, but not (3S)-L-serine 2 is enzymatically hydrolyzed. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis of topostins B567 and D654 (WB-3559D, flavolipin), DNA topoisomerase I inhibitors of bacterial origin
  作者：Takayuki Shioiri、Yoshihiro Terao、Naoko Irako、Toyohiko Aoyama

  DOI：10.1016/s0040-4020(98)00984-3

  日期：1998.12

  Topostins B567 (2b) and D654 (3b) (WB-3559D, flavolipin) have been efficiently synthesized from 1,10-decanediol (5) in 11 and 13 steps, respectively, involving an asymmetric hydrogenation of the beta-keto ester 14 using (R)-BINAP ruthenium bromide and a peptide coupling using diethyl phosphorocyanidate (DEPC, (EtO)(2)P(O)CN) as key steps. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• US5998668A
  申请人：——

  公开号：US5998668A

  公开（公告）日：1999-12-07
• Synthesis of sulfobacin A and B, new sulfonolipids isolated from Chryseobacterium sp.
  作者：Hirosato Takikawa、Shin-etsu Muto、Dai Nozawa、Akihiro Kayo、Kenji Mori

  DOI：10.1016/s0040-4039(98)01456-7

  日期：1998.9

  Sulfobacin A (1) and B (2), new sulfonolipids isolated from Chryseobacterium sp. as von Willebrand factor antagonists, were synthesized stereoselectively by starting from l-cysteine.

  硫杆菌素A（1）和B（2），新的磺脂从金黄葡萄菌中分离。von Willebrand因子拮抗剂，是从l-半胱氨酸开始立体选择性合成的。