(3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol | 862718-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol
• 英文别名: (1R)-1-[(4S,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl]-3-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]prop-2-yn-1-ol
• CAS: 862718-88-5
• 化学式: C₄₇H₅₆O₈
• 分子量: 748.957
• InChiKey: AATKBQZLZDPPRW-PCJBZQICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol 在 Lindlar's catalyst 吡啶 、 sodium azide 、 N-羟基-7-氮杂苯并三氮唑 、 氢气 、 sodium acetate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 对甲苯磺酰肼 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol
  参考文献：
  名称：

  A concise synthesis of (3S,4S,5R)-1-(α-d-galactopyranosyl)-3-tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH

  摘要：

  A concise and convergent synthesis of the C-glycoside analogue 2b of immunomodulating alpha-galactosylceramide OCH 1b starting from readily available 2,3,4,6-tetra-O-bensyl-D-galactose 3 and L-arabinose 6 is described. The synthesis features the nucleophilic addition of an alpha-ethynyl sugar 5 to the phytosphingosine-precursor aldehyde 9 and would be applicable to a variety of C-glycoside analogues of interest. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.069
• 作为产物：
  描述：

  2,3-O-isopropylidene-L-erythrofuranose 在 palladium on activated charcoal 正丁基锂 、 草酰氯 、 氢气 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 (3R,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-1-decyne-3,4,5-triol
  参考文献：
  名称：

  A concise synthesis of (3S,4S,5R)-1-(α-d-galactopyranosyl)-3-tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH

  摘要：

  A concise and convergent synthesis of the C-glycoside analogue 2b of immunomodulating alpha-galactosylceramide OCH 1b starting from readily available 2,3,4,6-tetra-O-bensyl-D-galactose 3 and L-arabinose 6 is described. The synthesis features the nucleophilic addition of an alpha-ethynyl sugar 5 to the phytosphingosine-precursor aldehyde 9 and would be applicable to a variety of C-glycoside analogues of interest. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.069

文献信息

• Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile
  作者：Tetsuya Toba、Kenji Murata、Junko Futamura、Kyoko Nakanishi、Bitoku Takahashi、Naohiro Takemoto、Minako Tomino、Takashi Nakatsuka、Seiichi Imajo、Megumi Goto、Takashi Yamamura、Sachiko Miyake、Hirokazu Annoura

  DOI：10.1016/j.bmc.2012.03.025

  日期：2012.5

  A series of truncated analogs of alpha-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-gamma ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. (C) 2012 Elsevier Ltd. All rights reserved.
• A concise synthesis of (3S,4S,5R)-1-(α-d-galactopyranosyl)-3-tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH
  作者：Tetsuya Toba、Kenji Murata、Takashi Yamamura、Sachiko Miyake、Hirokazu Annoura

  DOI：10.1016/j.tetlet.2005.05.069

  日期：2005.7

  A concise and convergent synthesis of the C-glycoside analogue 2b of immunomodulating alpha-galactosylceramide OCH 1b starting from readily available 2,3,4,6-tetra-O-bensyl-D-galactose 3 and L-arabinose 6 is described. The synthesis features the nucleophilic addition of an alpha-ethynyl sugar 5 to the phytosphingosine-precursor aldehyde 9 and would be applicable to a variety of C-glycoside analogues of interest. (c) 2005 Elsevier Ltd. All rights reserved.