(2S,3R,4E)-2-hexadecanoylamino-1-(4-C-methyl-β-D-glucopyranosyloxy)-4-octadecen-3-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R,4E)-2-hexadecanoylamino-1-(4-C-methyl-β-D-glucopyranosyloxy)-4-octadecen-3-ol
• 英文别名: N-[(E,2S,3R)-3-hydroxy-1-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-5-methyloxan-2-yl]oxyoctadec-4-en-2-yl]hexadecanamide
• 化学式: C₄₁H₇₉NO₈
• 分子量: 714.08
• InChiKey: AMWDNTOFCFEZHV-NHSILHBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  50
• 可旋转键数：
  33
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  棕榈酸酐 在 水 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 97.0h， 生成 (2S,3R,4E)-2-hexadecanoylamino-1-(4-C-methyl-β-D-glucopyranosyloxy)-4-octadecen-3-ol
  参考文献：
  名称：

  Synthesis of 4-C-methyl analogues of glucosylceramide

  摘要：

  Benzyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-methylene-alpha-D-xylo-hexopyranoside (3) was transformed with 3-chloroperoxybenzoic acid into the epoxides 4 and 5. Reductive opening of the epoxide moiety in 4 furnished benzyl 2,3,6-tri-O-benzyl-4-C-methyl-alpha-D-glucopyranoside (6); subsequent hydrogenolytic O-debenzylation, per-O-acetylation, selective removal of the anomeric O-acetyl group, and then treatment with trichloroacetonitrile in the presence of base afforded 2,3,4,6-tetra-O-acetyl-4-C-methyl-D-glucopyranosyl trichloroacetimidate (9). Reaction of 9 with the 3-O-benzoyl-azidosphingosines 10a,b in the presence of BF3 . OEt2 gave (2S,3R,4E)-2-azido-3-benzoyloxy-1-(2,3,4,6-tetra-O-acetyl-4-C-methyl-beta-D-glucopyranosyloxy)-4-octadecene (14a) and -4-dodecene (14b), respectively. Treatment of 14a,b with triphenylphosphine and the carboxylic acid anhydride in the presence of water and then with methanolic sodium methoxide gave the title compounds 16a,b.

  DOI：

  10.1016/0008-6215(92)80085-f

文献信息

• Synthesis of 4-C-methyl analogues of glucosylceramide
  作者：Michael Plewe、Konrad Sandhoff、Richard R. Schmidt

  DOI：10.1016/0008-6215(92)80085-f

  日期：1992.11

  Benzyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-methylene-alpha-D-xylo-hexopyranoside (3) was transformed with 3-chloroperoxybenzoic acid into the epoxides 4 and 5. Reductive opening of the epoxide moiety in 4 furnished benzyl 2,3,6-tri-O-benzyl-4-C-methyl-alpha-D-glucopyranoside (6); subsequent hydrogenolytic O-debenzylation, per-O-acetylation, selective removal of the anomeric O-acetyl group, and then treatment with trichloroacetonitrile in the presence of base afforded 2,3,4,6-tetra-O-acetyl-4-C-methyl-D-glucopyranosyl trichloroacetimidate (9). Reaction of 9 with the 3-O-benzoyl-azidosphingosines 10a,b in the presence of BF3 . OEt2 gave (2S,3R,4E)-2-azido-3-benzoyloxy-1-(2,3,4,6-tetra-O-acetyl-4-C-methyl-beta-D-glucopyranosyloxy)-4-octadecene (14a) and -4-dodecene (14b), respectively. Treatment of 14a,b with triphenylphosphine and the carboxylic acid anhydride in the presence of water and then with methanolic sodium methoxide gave the title compounds 16a,b.