methyl 4-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyluronate trichloroacetimidate | 406460-70-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyluronate trichloroacetimidate
• 英文别名: methyl 4-O-acetyl-2,3-di-O-benzyl-1-(trichloroacetimidoyloxy)-α-D-galactopyranuronate；methyl (2S,3R,4S,5R,6R)-3-acetyloxy-4,5-bis(phenylmethoxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate
• CAS: 406460-70-6
• 化学式: C₂₅H₂₆Cl₃NO₈
• 分子量: 574.842
• InChiKey: BXEFOABZVSQPLU-UKPGDCENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 4-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyluronate trichloroacetimidate 在 盐酸 、 三氟化硼 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 methyl (methyl 2,3-di-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：

  三氯乙腈 、 methyl 4-O-acetyl-2,3-di-O-benzyl-α/β-D-galactopyranuronate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到methyl 4-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyluronate trichloroacetimidate
  参考文献：
  名称：

  C-糖苷 D-半乳糖醛酸适合用作合成烯丙基 C-高-和鼠李糖-半乳糖醛酸模块的糖基受体

  摘要：

  甲基 2,3-di-O-benzyl-1-deoxy-1-(prop-2-enyl)-α-D-galactopyranuronate 和 benzyl 2,3-di-O-benzyl-1-deoxy-1-(prop -2-烯基)-α-D-吡喃半乳糖醛酸制备为糖基受体。糖基供体苄基 4-O-乙酰基-2,3-二-O-苄基-1-(三氯乙酰亚氨酰氧基)-α-D-吡喃半乳糖醛酸和苄基 4-O-乙酰基-2,3-二-O-苄基-1 -(三氯乙酰亚氨基酰氧基)-β-D-吡喃半乳糖基糖醛酸酯分别以98%和76%的产率合成。二糖甲基（甲基 4-O-乙酰基-2,3-二-O-苄基-α/β-D-吡喃半乳糖醛酸）-(1 →4)-2,3-二-O-苄基-1-脱氧-1 -(prop-2-enyl)-α-D-吡喃半乳糖和苄基(benzyl 4-O-acetyl-2,3-di-O-benzyl-α/β-D-galactopyranosyluronate)-(1

  DOI：

  10.3998/ark.5550190.0014.226