methyl 3,4-di-O-acetyl-2-O-benzyl-α-D-galactopyranosyluronate trichloroacetimidate | 406460-71-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-acetyl-2-O-benzyl-α-D-galactopyranosyluronate trichloroacetimidate
• 英文别名: methyl (2S,3R,4S,5R,6R)-3,4-diacetyloxy-5-phenylmethoxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate
• CAS: 406460-71-7
• 化学式: C₂₀H₂₂Cl₃NO₉
• 分子量: 526.755
• InChiKey: MNQJUFXXTWFWAL-QYXWGXCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 、 methyl 3,4-di-O-acetyl-2-O-benzyl-α-D-galactopyranosyluronate trichloroacetimidate 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， 以67%的产率得到methyl (methyl 3,4-di-O-acetyl-2-O-benzyl-α-D-galactopyranosyluronate)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  BLOCK SYNTHESIS WITH GALACTURONATE TRICHLOROACETIMIDATES1

  摘要：

  The disaccharide methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-alpha -L-rhamno pyranosyl)-(1 -->4)-(allyl 2,3-di-O-benzyl-beta -D-galactopyranosid)uronate (13) was obtained in an excellent yield of 88% using methyl (allyl 2,3-di-O-benzyl-beta -D-galactopyranosid)uronate (12) as the glycosyl acceptor and a slight excess Of the 1,2-di-O-acetyl-rhamnoglycosyl donor 5a. Disaccharide 13 is a key intermediate that can be used either as a glycosyl acceptor or glycosyl donor for the preparation of rhamnogalacturonan fragments. Here, introduction of the trichloroacetimidate function at the anomeric center gave the disaccharide glycosyl donor 28, which could be applied in a blockwise glycosylation reaction to form the L-Rha-alpha (1 -->4)-D-GalA-alpha (1 -->4)-D-GalA trisaccharide 29. Generally, on condition that no neighboring group effect influenced the reaction at the anomeric center of the alpha -trichloroacetimidate galacturonate glycosyl donors (20-22,28), alpha -glycosidic linkages were nearly exclusively formed, except in the case of the 4-O-methylgalactopyranosyluronate 22.

  DOI：

  10.1081/car-100108276
• 作为产物：
  描述：

  methyl (allyl 3,4-di-O-acetyl-2-O-benzyl-β-D-galactopyranosid)uronate 在 palladium dichloride sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 生成 methyl 3,4-di-O-acetyl-2-O-benzyl-α-D-galactopyranosyluronate trichloroacetimidate
  参考文献：
  名称：

  BLOCK SYNTHESIS WITH GALACTURONATE TRICHLOROACETIMIDATES1

  摘要：

  The disaccharide methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-alpha -L-rhamno pyranosyl)-(1 -->4)-(allyl 2,3-di-O-benzyl-beta -D-galactopyranosid)uronate (13) was obtained in an excellent yield of 88% using methyl (allyl 2,3-di-O-benzyl-beta -D-galactopyranosid)uronate (12) as the glycosyl acceptor and a slight excess Of the 1,2-di-O-acetyl-rhamnoglycosyl donor 5a. Disaccharide 13 is a key intermediate that can be used either as a glycosyl acceptor or glycosyl donor for the preparation of rhamnogalacturonan fragments. Here, introduction of the trichloroacetimidate function at the anomeric center gave the disaccharide glycosyl donor 28, which could be applied in a blockwise glycosylation reaction to form the L-Rha-alpha (1 -->4)-D-GalA-alpha (1 -->4)-D-GalA trisaccharide 29. Generally, on condition that no neighboring group effect influenced the reaction at the anomeric center of the alpha -trichloroacetimidate galacturonate glycosyl donors (20-22,28), alpha -glycosidic linkages were nearly exclusively formed, except in the case of the 4-O-methylgalactopyranosyluronate 22.

  DOI：

  10.1081/car-100108276