(2R,3R)-3-benzyloxy-2-tetradecyloctadecanoic acid | 108661-17-2

• 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: (2R,3R)-3-benzyloxy-2-tetradecyloctadecanoic acid
• 英文别名: (2R,3R)-3-phenylmethoxy-2-tetradecyloctadecanoic acid
• CAS: 108661-17-2
• 化学式: C₃₉H₇₀O₃
• 分子量: 586.983
• InChiKey: MWVGGOQWLWIEFO-XPSQVAKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  42
• 可旋转键数：
  32
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (2R,3R)-3-benzyloxy-2-tetradecyloctadecanoic acid 在 palladium on activated charcoal 氢气 作用下， 生成 (2R,3R)-3-hydroxy-2-tetradecyloctadecanoic acid
  参考文献：
  名称：

  使用1,2-不对称感应的非循环立体选择。首次全合成（+）-椰油酸

  摘要：

  描述了（+）-胭脂红酸（1）的第一全合成，该合成包括关键步骤，光学活性羰基化合物（8）的非对映选择性还原。

  DOI：

  10.1039/c39850000498
• 作为产物：
  描述：

  十四烷基碘化物 在 [(S)-2,2'-双(二苯基磷)-1,1'-联萘]二氯化钌(II) 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium hydride 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、6.86 MPa 条件下， 反应 82.42h， 生成 (2R,3R)-3-benzyloxy-2-tetradecyloctadecanoic acid
  参考文献：
  名称：

  Efficient Syntheses of a Series of Trehalose Dimycolate (TDM)/Trehalose Dicorynomycolate (TDCM) Analogues and Their Interleukin-6 Level Enhancement Activity in Mice Sera

  摘要：

  We found an IL-6 level-enhancing compound during our synthetic study of trehalose-6,6'-dimycolate (1, TDM, formerly called cord factor) analogues. TDM is a glycolipid distributed in the cell wall of Mycobacterium tuberculosis and shows significant antitumor activity based on an immunoadjuvant activity. However, due to its significant toxicity, TDM is not yet applicable for practical use. In 1993, Datta and Takayama reported the purification of trehalose-6,6'-dicorynomycolate (2c, TDCM) from Corynebacterium spp. We have previously reported the synthesis of four diastereomeric TDCMs and showed that the synthetic (2R,3R,2'R,3'R)-TDCM (2c, hereafter abbreviated RRRR-TDCM-C-14) is identical to natural TDCM; we also demonstrated that 2c and SSSS-TDCM-C-14 (3c) showed significant antitumor activity as well as inhibitory activity in experimental lung metastasis based on the immunoadjuvant activity. Furthermore, we found that the significant lethal toxicity in mice by TDM (1) was no longer observed with the shorter-chain analogues of TDCMs. Therefore, we have elucidated that the 2,3-antistereochemistry (RR or SS) of the fatty acid residue is promising for biological activities. The chain length of the fatty acid residue should also be important for the biological activity, and thus, we designed a general synthetic procedure for trehalose diesters with 2,3-antistereochemistry and a series of chain lengths by using Noyori's asymmetric reduction of beta,beta-ketoesters followed by antiselective alkylation according to Frater to give beta,beta-hydroxy alcohols as the key steps. Thus, we prepared trehalose diesters (TDCM) 2a-d, 3a-d, and 4a-d as well as monoesters (TMCM) 5a-d and 6a-d. Immunological activities of TDCMs and TMCMs were evaluated by determining IL-6 level enhancement in mouse serum, and we found that RRRR-TDCM-C-14 (2c) and RRSS-TDCM-C-14 (4c) showed significant IL-6 level enhancement activities.

  DOI：

  10.1021/jo062018j

文献信息

• Acyclic stereoselection using 1,2-asymmetric induction. The first total synthesis of (+)-corynomycolic acid
  作者：Yasunori Kitano、Yuichi Kobayashi、Fumie Sato

  DOI：10.1039/c39850000498

  日期：——

  The first total synthesis of (+)-corynomycolic acid (1), which includes as the key step, diastereoselective reduction of the optically active carbonyl compounds (8) is described.

  描述了（+）-胭脂红酸（1）的第一全合成，该合成包括关键步骤，光学活性羰基化合物（8）的非对映选择性还原。
• Efficient Syntheses of a Series of Trehalose Dimycolate (TDM)/Trehalose Dicorynomycolate (TDCM) Analogues and Their Interleukin-6 Level Enhancement Activity in Mice Sera
  作者：Mugio Nishizawa、Hirofumi Yamamoto、Hiroshi Imagawa、Véronique Barbier-Chassefière、Emmanuel Petit、Ichiro Azuma、Dulce Papy-Garcia

  DOI：10.1021/jo062018j

  日期：2007.3.1

  We found an IL-6 level-enhancing compound during our synthetic study of trehalose-6,6'-dimycolate (1, TDM, formerly called cord factor) analogues. TDM is a glycolipid distributed in the cell wall of Mycobacterium tuberculosis and shows significant antitumor activity based on an immunoadjuvant activity. However, due to its significant toxicity, TDM is not yet applicable for practical use. In 1993, Datta and Takayama reported the purification of trehalose-6,6'-dicorynomycolate (2c, TDCM) from Corynebacterium spp. We have previously reported the synthesis of four diastereomeric TDCMs and showed that the synthetic (2R,3R,2'R,3'R)-TDCM (2c, hereafter abbreviated RRRR-TDCM-C-14) is identical to natural TDCM; we also demonstrated that 2c and SSSS-TDCM-C-14 (3c) showed significant antitumor activity as well as inhibitory activity in experimental lung metastasis based on the immunoadjuvant activity. Furthermore, we found that the significant lethal toxicity in mice by TDM (1) was no longer observed with the shorter-chain analogues of TDCMs. Therefore, we have elucidated that the 2,3-antistereochemistry (RR or SS) of the fatty acid residue is promising for biological activities. The chain length of the fatty acid residue should also be important for the biological activity, and thus, we designed a general synthetic procedure for trehalose diesters with 2,3-antistereochemistry and a series of chain lengths by using Noyori's asymmetric reduction of beta,beta-ketoesters followed by antiselective alkylation according to Frater to give beta,beta-hydroxy alcohols as the key steps. Thus, we prepared trehalose diesters (TDCM) 2a-d, 3a-d, and 4a-d as well as monoesters (TMCM) 5a-d and 6a-d. Immunological activities of TDCMs and TMCMs were evaluated by determining IL-6 level enhancement in mouse serum, and we found that RRRR-TDCM-C-14 (2c) and RRSS-TDCM-C-14 (4c) showed significant IL-6 level enhancement activities.