6-O-(3,4,6-tri-O-allyl-α-D-lyxo-hexapyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside | 1401954-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(3,4,6-tri-O-allyl-α-D-lyxo-hexapyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
• 英文别名: 6-O-(3’,4’,6’-tri-O-allyl-2’-deoxy-α-D-galactopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside；(1S,2R,6R,8R,9S)-8-[[(2S,4R,5R,6R)-4,5-bis(prop-2-enoxy)-6-(prop-2-enoxymethyl)oxan-2-yl]oxymethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 1401954-57-1
• 化学式: C₂₇H₄₂O₁₀
• 分子量: 526.624
• InChiKey: XVQSUPWQLNJUDR-WTWMIZOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2R,3R,4R)-2-(羟基甲基)-3,4-二氢-2H-吡喃-3,4-二醇 在 1,3-双[3,5-双(三氟甲基)苯基]硫脲 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 18.0h， 生成 6-O-(3,4,6-tri-O-allyl-α-D-lyxo-hexapyranosyl)-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 organocatalyzed glycosylations – thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings
  作者：G. A. Bradshaw、A. C. Colgan、N. P. Allen、I. Pongener、M. B. Boland、Y. Ortin、E. M. McGarrigle

  DOI：10.1039/c8sc02788a

  日期：——

  Thiouracil catalyzes stereoselective glycosylations with galactals in loadings as low as 0.1 mol%.

  硫尿嘧啶在载体负载量低至0.1 mol％时，催化与半乳糖醛糖苷的立体选择性糖基化。
• 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。
• Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides
  作者：Jianbo Zhang、Youxian Dong、Madina Yuma、Yuling Mei、Nan Jiang、Guofang Yang、Zhongfu Wang

  DOI：10.1055/s-0040-1707098

  日期：2020.7

  acids, sugars, and phenol, and proceeds with excellent yield and high α-selectivity under mild conditions. The reaction proceeds readily on a gram scale, and its versatility is exemplified in the synthesis of oligosaccharides.

  开发了一种基于 Cu(II) 催化反应合成 2-脱氧-O-半乳糖苷的有效糖基化方法，无需额外配体。糖基化适用于不同的受保护糖基供体和广泛的受体，包括醇、氨基酸、糖和苯酚，并且在温和条件下以优异的收率和高α-选择性进行。该反应在克级规模上很容易进行，其多功能性体现在低聚糖的合成中。