2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-mannopyranose | 352020-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-mannopyranose
• 英文别名: Fguldclpykkibb-dkqogilzsa-；(2S,3S,4S,5R,6R)-2-ethenyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• CAS: 352020-77-0
• 化学式: C₃₆H₃₈O₆
• 分子量: 566.694
• InChiKey: FGULDCLPYKKIBB-DKQOGILZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-mannopyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到methyl O-(2',3',4',6'-tetra-O-benzyl-1'-C-vinyl-α-D-mannopyranosyl)-(1'->6)-2,3,4-tri-O-benzyl-α-D-glucoside
  参考文献：
  名称：

  A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides

  摘要：

  Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded alpha -stereoselectively and furnished the corresponding 1'-C-alkyl-alpha -disaccharides in 71-90% yields. The O-transglycosidations from the benzylated and acetylated methyl I-C-methyl-or-hexopyranosides to the corresponding 1'-C-methyl-alpha -O-disaccharides were also examined, respectively. These transglycosidations took place on alpha -stereoselectivity and provided the 1'-C-methyl-alpha -O-disaccharides as the sole products, implying that no neighboring group participation occured in the reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00321-0
• 作为产物：
  描述：

  乙烯基溴化镁 、 2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone 以 四氢呋喃 为溶剂， 反应 1.0h， 以82.4%的产率得到2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-mannopyranose
  参考文献：
  名称：

  A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides

  摘要：

  Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded alpha -stereoselectively and furnished the corresponding 1'-C-alkyl-alpha -disaccharides in 71-90% yields. The O-transglycosidations from the benzylated and acetylated methyl I-C-methyl-or-hexopyranosides to the corresponding 1'-C-methyl-alpha -O-disaccharides were also examined, respectively. These transglycosidations took place on alpha -stereoselectivity and provided the 1'-C-methyl-alpha -O-disaccharides as the sole products, implying that no neighboring group participation occured in the reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00321-0

文献信息

• Synthetic Approach to <i>exo</i>-Glycals from 1-<i>C</i>-Vinyl-<scp>d</scp>-glycopyranose Derivatives via an S_N1′-Substitution Mechanism
  作者：Takashi Yamanoi、Yukari Nara、Sho Matsuda、Yoshiki Oda、Akihiro Yoshida、Kaname Katsuraya、Mikio Watanabe

  DOI：10.1055/s-2007-970751

  日期：2007.3

  describes a novel synthetic approach to exo- glycals from 1-C-vinyl-D-glycopyranose derivatives via the SN1¢- type substitution mechanism. The reaction of the 2,3,4,6-tetra-O- benzyl-1-C-vinyl-a-D-glycopyranose derivatives with several tri- methylsilylated nucleophiles was investigated. The reactions in dichloromethane-acetonitrile (1:1) at -78 °C in the presence of 20 mol% trimethylsilyl trifluoromethanesulfonate

  本文描述了一种通过 SN1 型取代机制从 1-C-乙烯基-D-吡喃葡萄糖衍生物合成外切糖的新方法。研究了 2,3,4,6-四-O-苄基-1-C-乙烯基-aD-吡喃葡萄糖衍生物与几种三甲基甲硅烷基化亲核试剂的反应。使用烯丙基三甲基硅烷和甲硅烷基烯醇醚作为亲核试剂，在 -78 °C 的二氯甲烷-乙腈 (1:1) 中，在 20 mol% 三氟甲磺酸三甲基甲硅烷基酯的存在下进行反应，立体选择性地以良好的收率提供了 Z-外-糖基衍生物。
• A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides
  作者：Xiaoliu Li、Hiro Ohtake、Hideyo Takahashi、Shiro Ikegami

  DOI：10.1016/s0040-4020(01)00321-0

  日期：2001.5

  Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded alpha -stereoselectively and furnished the corresponding 1'-C-alkyl-alpha -disaccharides in 71-90% yields. The O-transglycosidations from the benzylated and acetylated methyl I-C-methyl-or-hexopyranosides to the corresponding 1'-C-methyl-alpha -O-disaccharides were also examined, respectively. These transglycosidations took place on alpha -stereoselectivity and provided the 1'-C-methyl-alpha -O-disaccharides as the sole products, implying that no neighboring group participation occured in the reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.