[(2R,3R,4S,5S,6R)-2-[(2R)-2,3-dihexadecoxypropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] acetate | 189209-56-1

• 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: [(2R,3R,4S,5S,6R)-2-[(2R)-2,3-dihexadecoxypropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] acetate
• CAS: 189209-56-1
• 化学式: C₄₃H₈₄O₉
• 分子量: 745.135
• InChiKey: SQYXLFZAGGJFOS-LSTMTGNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  52
• 可旋转键数：
  39
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 [(2R,3R,4S,5S,6R)-2-[(2R)-2,3-dihexadecoxypropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] acetate 在 吡啶 作用下， 以95%的产率得到Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((R)-2,3-bis-hexadecyloxy-propoxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  An efficient stereoselective synthesis of enantiomerically pure mono- and di-O-hexadecyl-β-d-glucosylglycerol ethers by epoxidation of an allyl β-d-glucopyranoside asymmetrically induced by the glucide moiety

  摘要：

  1-O-Hexadecyl and 1,2-di-O-hexadecyl-3-O-(beta-D-glucopyranosyl)-sn-glycerol ethers were obtained by regiospecific opening of the oxirane ring of the 2',3'-epoxypropyl 2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranoside synthetized by stereoselective epoxidation of the corresponding allyl 3,4,6-tri-O-benzyl-beta-D-glucopyranoside asymmetrically induced by the glucide moiety. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00041-4
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-2-[(2R)-3-hexadecoxy-2-hydroxypropoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate 在 palladium on activated charcoal Proton Sponge 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 147.0h， 生成 [(2R,3R,4S,5S,6R)-2-[(2R)-2,3-dihexadecoxypropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] acetate
  参考文献：
  名称：

  An efficient stereoselective synthesis of enantiomerically pure mono- and di-O-hexadecyl-β-d-glucosylglycerol ethers by epoxidation of an allyl β-d-glucopyranoside asymmetrically induced by the glucide moiety

  摘要：

  1-O-Hexadecyl and 1,2-di-O-hexadecyl-3-O-(beta-D-glucopyranosyl)-sn-glycerol ethers were obtained by regiospecific opening of the oxirane ring of the 2',3'-epoxypropyl 2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranoside synthetized by stereoselective epoxidation of the corresponding allyl 3,4,6-tri-O-benzyl-beta-D-glucopyranoside asymmetrically induced by the glucide moiety. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00041-4