ethyl (3R)-hydroxy-15-methylhexadecanoate | 212838-94-3

• 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 (3R)-hydroxy-15-methylhexadecanoate
• 英文别名: ethyl (3R)-3-hydroxy-15-methylhexadecanoate
• CAS: 212838-94-3
• 化学式: C₁₉H₃₈O₃
• 分子量: 314.509
• InChiKey: DCDICQDUOBABJF-GOSISDBHSA-N

物化性质

• 沸点：
  413.3±18.0 °C(Predicted)
• 密度：
  0.914±0.06 g/cm3(Predicted)

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 (3R)-hydroxy-15-methylhexadecanoate 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 TEA 、 双氧水 、 焦碳酸二乙酯 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 22.0h， 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：

  Total synthesis of sulfobacin A (flavocristamide B)

  摘要：

  Sulfobacin A (1), a novel von Willebrand factor receptor antagonist isolated from the culture broth of Chryseobacterium sp. NR 2993, was efficiently synthesized for the first time. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01177-0
• 作为产物：
  描述：

  magnesium,2-methylbutane,bromide 在 ruthenium trichloride sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 氯化亚砜 、 dilithium tetrachlorocuprate 、 potassium carbonate 、 二甲基亚砜 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 50.83h， 生成 ethyl (3R)-hydroxy-15-methylhexadecanoate
  参考文献：
  名称：

  An efficient total synthesis of sulfobacin A

  摘要：

  A short and efficient enantioselective synthesis of sulfobacin A has been achieved using the Sharpless asymmetric dihydroxylation and the regiospecific nucleophilic opening of a cyclic sulfate as the key steps. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.137

文献信息

• 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.
• An Efficient Synthesis of Sulfobacin A (Flavocristamide B), Sulfobacin B, and Flavocristamide A
  作者：Takayuki Shioiri、Naoko Irako

  DOI：10.1016/s0040-4020(00)00768-7

  日期：2000.11

  Sulfobacin A (flavocristamide B, 1), sulfobacin B (2), and flavocristamide A (3), biologically active sulfonolipids, have been efficiently synthesized utilizing the asymmetric aldol reaction of the Schiff base 8 derived from glycine eater and (+)-2-hydroxy-3-pinanone (HyPN). (C) 2000 Elsevier Science 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.
• An efficient total synthesis of sulfobacin A
  作者：Priti Gupta、S. Vasudeva Naidu、Pradeep Kumar

  DOI：10.1016/j.tetlet.2004.10.137

  日期：2004.12

  A short and efficient enantioselective synthesis of sulfobacin A has been achieved using the Sharpless asymmetric dihydroxylation and the regiospecific nucleophilic opening of a cyclic sulfate as the key steps. (C) 2004 Elsevier Ltd. All rights reserved.
• Total synthesis of sulfobacin A (flavocristamide B)
  作者：Naoko Irako、Takayuki Shioiri

  DOI：10.1016/s0040-4039(98)01177-0

  日期：1998.8

  Sulfobacin A (1), a novel von Willebrand factor receptor antagonist isolated from the culture broth of Chryseobacterium sp. NR 2993, was efficiently synthesized for the first time. (C) 1998 Elsevier Science Ltd. All rights reserved.