(2S,3R,4S,5S,6R)-2-[(2S,3S,4R)-2-azido-3,4-bis(phenylmethoxy)octadec-5-ynoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane | 947747-26-4

• 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: (2S,3R,4S,5S,6R)-2-[(2S,3S,4R)-2-azido-3,4-bis(phenylmethoxy)octadec-5-ynoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 947747-26-4
• 化学式: C₆₆H₇₉N₃O₈
• 分子量: 1042.37
• InChiKey: SBHKDBACQVTSNN-FGWKQXODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.7
• 重原子数：
  77
• 可旋转键数：
  35
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6R)-2-[(2S,3S,4R)-2-azido-3,4-bis(phenylmethoxy)octadec-5-ynoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Concise syntheses of immunostimulating glycolipids, α-galactosyl ceramides

  摘要：

  alpha-Galactosylceramides (alpha-GalCers) are well known as immunostimulating agents having therapeutic potential. To facilitate the synthesis of alpha-GalCers and their derivatives, a novel and convergent strategy was designed, which is expected to be versatile for the preparation of a variety of analogues in a diversity-oriented fashion. As an initial demonstration of our strategy, KRN7000 and OCH were synthesized in eight steps from a common intermediate, which is easily obtainable in a multi-gram scale. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.161
• 作为产物：
  描述：

  (2R,3R)-3-(benzyloxy)-4-(naphthalen-2-ylmethoxy)butane-1,2-diol 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 正丁基锂 、 sodium azide 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 2-甲基-2-丁烯 、 dimethyl sulfide borane 、 4-甲基苯磺酸吡啶 、 四丁基碘化铵 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟甲烷磺酸甲酯 、 (R)-(+)-tetrahydro-1-methyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 生成 (2S,3R,4S,5S,6R)-2-[(2S,3S,4R)-2-azido-3,4-bis(phenylmethoxy)octadec-5-ynoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
  参考文献：
  名称：

  Concise syntheses of immunostimulating glycolipids, α-galactosyl ceramides

  摘要：

  alpha-Galactosylceramides (alpha-GalCers) are well known as immunostimulating agents having therapeutic potential. To facilitate the synthesis of alpha-GalCers and their derivatives, a novel and convergent strategy was designed, which is expected to be versatile for the preparation of a variety of analogues in a diversity-oriented fashion. As an initial demonstration of our strategy, KRN7000 and OCH were synthesized in eight steps from a common intermediate, which is easily obtainable in a multi-gram scale. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.161

文献信息

• Concise syntheses of immunostimulating glycolipids, α-galactosyl ceramides
  作者：Takashi Tsujimoto、Yukishige Ito

  DOI：10.1016/j.tetlet.2007.05.161

  日期：2007.7

  alpha-Galactosylceramides (alpha-GalCers) are well known as immunostimulating agents having therapeutic potential. To facilitate the synthesis of alpha-GalCers and their derivatives, a novel and convergent strategy was designed, which is expected to be versatile for the preparation of a variety of analogues in a diversity-oriented fashion. As an initial demonstration of our strategy, KRN7000 and OCH were synthesized in eight steps from a common intermediate, which is easily obtainable in a multi-gram scale. (C) 2007 Elsevier Ltd. All rights reserved.