(2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol | 956038-73-6

• 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-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol
• 英文别名: (2S,3S,4R)-2-azido-8-methyl-3-phenylmethoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxynon-5-yn-4-ol
• CAS: 956038-73-6
• 化学式: C₅₁H₅₇N₃O₈
• 分子量: 840.029
• InChiKey: NPBRYPGAZIYUAO-REBVYZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  62
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 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-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol 在 吡啶 、 硫化氢 、 sodium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 52.0h， 生成 (2S,3S,4R)-3-benzyloxy-2-docosanoylamino-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-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：

  (+)-2,3-O-亚苄基-D-苏糖醇 在 吡啶 、 sodium azide 、 硼烷四氢呋喃络合物 、 草酰氯 、 四溴化碳 、 N-甲基麻黄碱 、 四丁基氟化铵 、 zinc trifluoromethanesulfonate 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 232.0h， 生成 (2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-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

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.