2,3,4-tri-O-acetyl-β-L-arabinopyranosyl chloride | 69308-56-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-β-L-arabinopyranosyl chloride
• 英文别名: 2,3,4-Tri-O-acetyl-β-L-arabopyranosyl-chlorid；[(3S,4S,5R,6S)-4,5-diacetyloxy-6-chlorooxan-3-yl] acetate
• CAS: 69308-56-1
• 化学式: C₁₁H₁₅ClO₇
• 分子量: 294.689
• InChiKey: JWDUFIUUDGFMTM-UKKRHICBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-β-L-arabinopyranosyl chloride 、 甲基 6-O-[二甲基(2-甲基-2-丙基)硅烷基]-alpha-D-吡喃甘露糖苷 在 diphenylborate ethanolamine ester 、 silver(l) oxide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以86%的产率得到methyl 6-O-tert-butyldimethylsilyl-3-O-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Regioselective Activation of Glycosyl Acceptors by a Diarylborinic Acid-Derived Catalyst

  摘要：

  A derivative of diphenylborinic add promotes catalytic, regioselective Koenigs-Knorr glycosylations of carbohydrate derivatives bearing multiple secondary hydroxyl groups. Robust levels of selectivity for the equatorial OH group of cis-1,2-diol motifs are demonstrated in reactions of seven acceptors derived from galactose, mannose, fucose, and arabinose using a variety of glycosyl halide donors. Catalyst control presents a new means of generating defined glycosidic linkages from unprotected or minimally protected carbohydrate feedstocks.

  DOI：

  10.1021/ja2062715
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-L-arabinopyranose 在 三聚氯氰 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2,3,4-tri-O-acetyl-β-L-arabinopyranosyl chloride
  参考文献：
  名称：

  Regioselective Activation of Glycosyl Acceptors by a Diarylborinic Acid-Derived Catalyst

  摘要：

  A derivative of diphenylborinic add promotes catalytic, regioselective Koenigs-Knorr glycosylations of carbohydrate derivatives bearing multiple secondary hydroxyl groups. Robust levels of selectivity for the equatorial OH group of cis-1,2-diol motifs are demonstrated in reactions of seven acceptors derived from galactose, mannose, fucose, and arabinose using a variety of glycosyl halide donors. Catalyst control presents a new means of generating defined glycosidic linkages from unprotected or minimally protected carbohydrate feedstocks.

  DOI：

  10.1021/ja2062715

文献信息

• Indium(III) Triflate–Mediated One-Step Preparation of Glycosyl Halides from Free Sugars
  作者：Santosh Kumar Giri、K. P. Ravindranathan Kartha

  DOI：10.1080/00397910903419886

  日期：2010.10.20

  In(OTf)3 has been found to be an efficient catalyst for the direct conversion of reducing sugars to their respective acylated glycosyl halides in good yields under mild conditions. The glycosyl halides so obtained can be converted to alkyl glycosides in the same pot by reacting them with the respective alcohols in good yield.