1-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-2-propene | 271246-08-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-2-propene
• 英文别名: 3-C-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)propene；(2R,3S,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-2-enyloxan-3-ol
• CAS: 271246-08-3
• 化学式: C₃₀H₃₄O₅
• 分子量: 474.597
• InChiKey: UYWKXHISDGPRTR-IXYVTWBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-2-propene 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 乙烯 、 2,4,6-三氯苯甲酰氯 、 palladium 10% on activated carbon 、 水 、 三正丁基氢锡 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 、 环己烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 、 苯 为溶剂， 反应 97.0h， 生成 CRONY 101
  参考文献：
  名称：

  Intramolecular Nitrogen Delivery for the Synthesis of C-Glycosphingolipids. Application to the C-Glycoside of the Immunostimulant KRN7000

  摘要：

  The key reaction in this approach to C-glycosphingolipids is the stereoselective iodocyclization of a sugar-linked homoallylic carbonimidothioate. E and Z reaction substrates were assembled in a convergent fashion via an alkene metathesis strategy and exhibited the same alkene facial selectivity in the iodocyclization irrespective of alkene geometry, although the E alkene was found to be less reactive.

  DOI：

  10.1021/ol5002686
• 作为产物：
  描述：

  3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene 在 碘 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-2-propene
  参考文献：
  名称：

  Stereoselective synthesis of α-C-glycosides of N-acetylgalactosamine

  摘要：

  Attempts to synthesise alpha-C-glycosides of N-acetylgalactosamine by selective deprotection at C-2' of allyl alpha-C-galactoside 1 and subsequent amination failed, but opened the way to alpha-C-talopyranosides. The synthesis of alpha-C-glycosides of N-acetylgalactosamine was performed from allyl alpha-C-glucopyranoside 9, which was regioselectively deprotected, stereoselectively aminated at C-2', and finally epimerised at C-4'. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00480-2

文献信息

• Stereoselective Synthesis of 2-<i>C</i>-Acetonyl-2-Deoxy-<scp>d</scp>-Galactosides using 1,2-Cyclopropaneacetylated Sugar as Novel Glycosyl Donor
  作者：Qiang Tian、Liyan Xu、Xiaofeng Ma、Wei Zou、Huawu Shao

  DOI：10.1021/ol902732w

  日期：2010.2.5

  1,2-Cyclopropaneacetylated sugar is an effective glycosyl donor, which reacted with various glycosyl acceptors including monosaccharides, amino acids and other alcohols in the presence of BF3•OEt2 or TMSOTf. The glycosylation is stereoselective in favor of β-anomeric products with BF3•OEt2 as catalyst, whereas TMSOTf-catalyzed glycosylation prefers the α-anomeric products. 2-C-Acetonyl-2-deoxy-d-galactosides

  1,2-环丙烷乙酰化糖是一种有效的糖基供体，在BF 3 •OEt 2或TMSOTf存在下，它可以与各种糖基受体（包括单糖，氨基酸和其他醇）反应。糖基化具有立体选择性，有利于以BF 3 •OEt 2为催化剂的β-异头物，而TMSOTf催化的糖基化则更优选α-异头物。2- Ç -Acetonyl -2-脱氧d以良好产率得到-galactosides。
• C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates
  作者：Ahmad S. Altiti、David R. Mootoo

  DOI：10.1016/j.carres.2015.02.005

  日期：2015.4

  The iodocyclization of homoallylic trichloroacetimidates derived from alpha-C-allyl galactoside were investigated. In line with the stereochemical trend observed for less substituted non-glycosylated frameworks, E and Z substrates delivered stereoselectively the 1,3-anti and 1,3-syn amino alcohol motifs, respectively. These products are advanced precursors to C-glycosides of the potent immunostimulatory

  研究了源自α-C-烯丙基半乳糖苷的高烯丙基三氯乙酰亚胺酯的碘环化。与较少取代的非糖基化框架观察到的立体化学趋势一致，E 和 Z 底物分别立体选择性地递送 1,3-anti 和 1,3-syn 氨基醇基序。这些产品是强效免疫刺激糖脂 KRN7000 的 C-糖苷的高级前体。
• One-Pot Synthesis of 2-<i>C</i>-Branched Glycosyl Triazoles by Integrating 1,2-Cyclopropanated Sugar Ring-Opening Azidation and CuAAC Reaction
  作者：Zhongke Shen、Qin Tang、Wei Jiao、Huawu Shao、Xiaofeng Ma

  DOI：10.1021/acs.joc.2c02390

  日期：2022.12.16
• Intramolecular Nitrogen Delivery for the Synthesis of C-Glycosphingolipids. Application to the C-Glycoside of the Immunostimulant KRN7000
  作者：Ahmad S. Altiti、David R. Mootoo

  DOI：10.1021/ol5002686

  日期：2014.3.7

  The key reaction in this approach to C-glycosphingolipids is the stereoselective iodocyclization of a sugar-linked homoallylic carbonimidothioate. E and Z reaction substrates were assembled in a convergent fashion via an alkene metathesis strategy and exhibited the same alkene facial selectivity in the iodocyclization irrespective of alkene geometry, although the E alkene was found to be less reactive.
• Stereoselective synthesis of α-C-glycosides of N-acetylgalactosamine
  作者：Laura Cipolla、Barbara La Ferla、Luigi Lay、Francesco Peri、Francesco Nicotra

  DOI：10.1016/s0957-4166(99)00480-2

  日期：2000.1

  Attempts to synthesise alpha-C-glycosides of N-acetylgalactosamine by selective deprotection at C-2' of allyl alpha-C-galactoside 1 and subsequent amination failed, but opened the way to alpha-C-talopyranosides. The synthesis of alpha-C-glycosides of N-acetylgalactosamine was performed from allyl alpha-C-glucopyranoside 9, which was regioselectively deprotected, stereoselectively aminated at C-2', and finally epimerised at C-4'. (C) 2000 Elsevier Science Ltd. All rights reserved.