6-(2,3,4-tri-O-benzoyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside | 1401954-93-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(2,3,4-tri-O-benzoyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-2-[[(2S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl] benzoate
• CAS: 1401954-93-5
• 化学式: C₆₆H₇₀O₁₈
• 分子量: 1151.27
• InChiKey: VVNHBPIUCRFKSA-XYPWNACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  84
• 可旋转键数：
  25
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  190
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  phenyl 2,3,4-tri-O-benzoyl-6-O-(2-deoxy-3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-thioglucopyranoside 、 双丙酮半乳糖 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以333 mg的产率得到6-(2,3,4-tri-O-benzoyl-6-O-(3,4,6-tri-O-benzyl-α-D-lyxo-hexapyranosyl)-β-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  α-Selective Organocatalytic Synthesis of 2-Deoxygalactosides

  摘要：

  Alpha rules: A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2-deoxymonosaccharide moiety. The reaction is highly stereoselective for α-linkages and proceeds by way of a syn-addition mechanism.

  DOI：

  10.1002/anie.201204505

文献信息

• Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis
  作者：Gaoyuan Zhao、Ting Wang

  DOI：10.1002/anie.201800909

  日期：2018.5.22

  The direct, photoacid‐catalyzed synthesis of 2‐deoxyglycosides from glycals is reported. A series of phenol‐conjugated acridinium‐based organic photoacids were rationally designed, synthesized, and studied alongside the commercially available phenolic catalyst eosin Y. In the presence of such a photoacid catalyst and light, synthetic glycals were activated and coupled with a range of alcohols to afford

  据报道，由糖类直接，光酸催化合成了2-脱氧糖苷。与市售的酚催化剂曙红Y一起，合理设计，合成和研究了一系列基于酚共轭啶基的有机光酸。在这种光酸催化剂和光的存在下，合成糖被活化并与多种醇偶联以高收率和优异的α-选择性提供2-脱氧糖苷。