(2S,3S,4R)-2-azido-3-benzyloxy-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)octadec-5-yn-4-ol | 947747-25-3

• 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: (2S,3S,4R)-2-azido-3-benzyloxy-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)octadec-5-yn-4-ol
• 英文别名: (2S,3S,4R)-2-azido-3-phenylmethoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoctadec-5-yn-4-ol
• CAS: 947747-25-3
• 化学式: C₅₉H₇₃N₃O₈
• 分子量: 952.244
• InChiKey: SCIXZLYKEDLNOQ-PPKLLBEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.7
• 重原子数：
  70
• 可旋转键数：
  32
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-azido-3-benzyloxy-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)octadec-5-yn-4-ol 在 吡啶 、 硫化氢 作用下， 以 水 为溶剂， 反应 48.0h， 生成 (2S,3S,4R)-2-amino-3-benzyloxy-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)octadec-5-yn-4-ol
  参考文献：
  名称：

  A General and Stereoselective Route to α- or β-Galactosphingolipids via a Common Four-Carbon Building Block

  摘要：

  [GRAPHICS]A general synthetic strategy toward alpha- or beta-galactosylceramides and their analogues from 3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)butane- 1,2,4-triol is described. The key steps for the installation of the main lipid chain are either a diasteroselective alkynylation reaction yielding the 4R stereocenter of phytosphingosine or a Wittig olefination generating the trans double bond of sphingosine. The methodology allows the preparation of different glycolipids with variations in the structure of the sphingoid base. In particular, three alpha-GalCer-related compounds have been synthesized and evaluated for their ability to activate CD1d-restricted T-cells.

  DOI：

  10.1021/jo070849z
• 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 、 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,3S,4R)-2-azido-3-benzyloxy-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)octadec-5-yn-4-ol
  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

• A General and Stereoselective Route to α- or β-Galactosphingolipids via a Common Four-Carbon Building Block
  作者：Pamela Matto、Emilia Modica、Laura Franchini、Federica Facciotti、Lucia Mori、Gennaro De Libero、Grazia Lombardi、Silvia Fallarini、Luigi Panza、Federica Compostella、Fiamma Ronchetti

  DOI：10.1021/jo070849z

  日期：2007.9.1

  [GRAPHICS]A general synthetic strategy toward alpha- or beta-galactosylceramides and their analogues from 3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)butane- 1,2,4-triol is described. The key steps for the installation of the main lipid chain are either a diasteroselective alkynylation reaction yielding the 4R stereocenter of phytosphingosine or a Wittig olefination generating the trans double bond of sphingosine. The methodology allows the preparation of different glycolipids with variations in the structure of the sphingoid base. In particular, three alpha-GalCer-related compounds have been synthesized and evaluated for their ability to activate CD1d-restricted T-cells.
• 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.