phenyl 6-O-benzyl-1-thio-β-D-glucopyranoside | 136882-37-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-((Benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triol；(2R,3S,4S,5R,6S)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxane-3,4,5-triol
• CAS: 136882-37-6
• 化学式: C₁₉H₂₂O₅S
• 分子量: 362.447
• InChiKey: WMSWWJHIVWFJLE-FQBWVUSXSA-N

物化性质

• 熔点：
  96-101°C
• 沸点：
  565.1±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  phenyl 6-O-benzyl-1-thio-β-D-glucopyranoside 在 三氟甲磺酸 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 phenyl 2,3,4-tri-O-benzyl-6-O-(6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  “Super Armed” Glycosyl Donors:  Conformational Arming of Thioglycosides by Silylation

  摘要：

  Glycosyl donors protected with bulky silyl protective groups (tert-butyldimethylsilyl, TBS), on the 2-, 3-, and 4-OH groups were found to have superior reactivity compared with benzylated thioglucosides. The enhanced reactivity is explained by the stereoelectronic effects associated with the conformational change induced by the silylation. A TBS silylated thioglucoside donor has axial OR groups, whereas a benzylated thioglucoside has equatorial OR groups, leading to much more favorable charge-dipole interactions in the transition state. This concept could be used to create "super armed" glucosyl, mannosyl, rhamnosyl, and galactosyl donors, which could cross-couple with the armed acceptors, phenyl 2,3,4-tri-O- benzyl-beta-D-thioglucoside or phenyl 2,3,6-tri-O-benzyl-beta-D-thioglucoside, to give the corresponding armed disaccharides in good to excellent yields.

  DOI：

  10.1021/ja071955l
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 1-硫代-b-D-吡喃葡萄糖苷对甲苯酯 生成 phenyl 6-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  “Super Armed” Glycosyl Donors:  Conformational Arming of Thioglycosides by Silylation

  摘要：

  Glycosyl donors protected with bulky silyl protective groups (tert-butyldimethylsilyl, TBS), on the 2-, 3-, and 4-OH groups were found to have superior reactivity compared with benzylated thioglucosides. The enhanced reactivity is explained by the stereoelectronic effects associated with the conformational change induced by the silylation. A TBS silylated thioglucoside donor has axial OR groups, whereas a benzylated thioglucoside has equatorial OR groups, leading to much more favorable charge-dipole interactions in the transition state. This concept could be used to create "super armed" glucosyl, mannosyl, rhamnosyl, and galactosyl donors, which could cross-couple with the armed acceptors, phenyl 2,3,4-tri-O- benzyl-beta-D-thioglucoside or phenyl 2,3,6-tri-O-benzyl-beta-D-thioglucoside, to give the corresponding armed disaccharides in good to excellent yields.

  DOI：

  10.1021/ja071955l

文献信息

• Synthesis of novel disaccharides based on glycosyltransferases: β1,4galactosyltransferase
  作者：Chi-Huey Wong、Thomas Krach、Christine Gautheron-Le Narvor、Yoshitaka Ichikawa、Gary C. Look、Federico Gaeta、David Thompson、K.C. Nicolaou

  DOI：10.1016/s0040-4039(00)93482-8

  日期：1991.9

  Beta-1,4Galactosyltransferase and beta-galactosidase have been investigated with regard to their acceptor specificity and used in the synthesis of galactosides using 5-thioglucose, deoxyazaglucose, glucal, modified N-acetylglucosamine and glucose derivatives as acceptors.
• Selective Protection of Hydroxy Group at C6 Position of Glucose Derivatives
  作者：Yoshiharu Sawada、Naoki Nanboku、Emiko Yanase、Shin-ichi Nakatsuka

  DOI：10.1515/hc.2010.16.1.21

  日期：2010.1

  6-O-Benzyl derivatives and 6-O-toluoyl derivatives, 2a-f and 3a-f, were prepared in high yields from glucose derivatives 1a-f through multi-level anion formation using an excess of sodium hydride (4 eq.).