(2S,3S)-3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)-4-O-(thexyldimethylsilyl)butane-1,2,4-triol | 956038-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)-4-O-(thexyldimethylsilyl)butane-1,2,4-triol
• 英文别名: [(2S,3S)-2-azido-4-[(4-methoxyphenyl)methoxy]-3-phenylmethoxybutoxy]-(2,3-dimethylbutan-2-yl)-dimethylsilane
• CAS: 956038-70-3
• 化学式: C₂₇H₄₁N₃O₄Si
• 分子量: 499.726
• InChiKey: MXQYWFXPZOIBSD-IZZNHLLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)-4-O-(thexyldimethylsilyl)butane-1,2,4-triol 在 吡啶 、 草酰氯 、 四溴化碳 、 N-甲基麻黄碱 、 硫化氢 、 四丁基氟化铵 、 sodium acetate 、 zinc trifluoromethanesulfonate 、 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 、 甲苯 为溶剂， 反应 251.0h， 生成 (2S,3S,4R)-3-benzyloxy-2-docosanoylamino-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-O-benzyl-4-O-(4-methoxybenzyl)-1-O-(thexyldimethylsilyl)butane-1,2,3,4-tetrol 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (2S,3S)-3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)-4-O-(thexyldimethylsilyl)butane-1,2,4-triol
  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

• Total Synthesis of Terpioside B
  作者：Kazuki Inaba、Masato Endo、Naoto Iibuchi、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1002/chem.202002878

  日期：2020.8.12

  The first total synthesis of terpioside B (1 ) has been accomplished. Key steps include the stereoselective installments of a set of challenging 1,2‐cis‐glycosidic linkages. Thus, α(1,4)‐linked d ‐galactoside was effectively constructed from a 1,2‐anhydrogalactose donor and an unprotected 1,6‐anhydrogalactose acceptor by using a boron‐mediated aglycon delivery (BMAD) method. In addition, α‐l ‐fucofuranosides

  已经完成了萜品甙B（1）的第一个全合成。关键步骤包括一组具有挑战性的1,2-顺式-糖苷键的立体选择性部分。因此，通过硼介导的糖苷配基传递（BMAD）方法，由1,2-脱水半乳糖供体和未保护的1,6-脱水半乳糖受体有效构建了α（1,4）-连接的d-半乳糖苷。此外，α- 1-呋喃呋喃糖苷是立体选择性的，并通过远程的组1,2-顺-α-立体选择性糖基化同时构建。
• 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.