O--(2->6)-3,4-di-O-acetyl-2-azido-2-deoxy-D-galactopyranose trichloroacetimidate | 164203-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O--(2->6)-3,4-di-O-acetyl-2-azido-2-deoxy-D-galactopyranose trichloroacetimidate
• CAS: 164203-08-1
• 化学式: C₃₂H₄₂Cl₃N₅O₁₉
• 分子量: 907.067
• InChiKey: GXRQUQXEJJZJAA-QSPXIDFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  59.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  322.73
• 氢给体数：
  2.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  O--(2->6)-3,4-di-O-acetyl-2-azido-2-deoxy-D-galactopyranose trichloroacetimidate 在 palladium on activated charcoal 、 Lindlar's catalyst sodium hydroxide 、 molecular sives AW 、 氢气 、 TMSOTf 作用下， 以 吡啶 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 24.67h， 生成 (2R,4S,5R,6R)-5-乙酰氨基-2-[[(2R,3R,4R,5R,6S)-5-乙酰氨基-6-[(2S)-2-氨基-3-羟基-3-氧代丙氧基]-3,4-二羟基四氢吡喃-2-基]甲氧基]-4-羟基-6-[(1R,2R)-1,2,3-三羟基丙基]四氢吡喃-2-羧酸
  参考文献：
  名称：

  Total synthesis of 3-O-[2-acetamido-6-O-(N-acetyl-α-d-neuraminyl)-2-deoxy-α-d-galactosyl]-l-serine and a stereoisomer

  摘要：

  O-(5-Acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2- nonulopyranoxylonic acid)-(2----6)-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-(1----3) -L-serine, a structural unit occurring in various submaxillary mucins, was synthesized for the first time by using O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D- galacto-2-nonulopyranosyl)onate]-(2----6)-3,4-di-O-acetyl-2- azido-2-deoxy-D- galactopyranosyl trichloroacetimidate (13) and N-(benzyloxycarbonyl)-L-serine benzyl ester as the key intermediates. The trichloroacetimidate 13 was prepared by starting from two monosaccharide synthons, namely, allyl 2-azido-2-deoxy-beta-D-galactopyranoside and methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-beta-D- galacto-2-nonulopyranosyl chloride)onate, which were coupled in the presence of silver triflate in tetrahydrofuran to give the desired alpha-(2----6)-linked disaccharide in moderate selectivity.

  DOI：

  10.1016/s0008-6215(00)90853-x
• 作为产物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 molecular sives 4A 、 sodium acetate 、 silver trifluoromethanesulfonate 、 potassium carbonate 、 palladium dichloride 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 47.0h， 生成 O--(2->6)-3,4-di-O-acetyl-2-azido-2-deoxy-D-galactopyranose trichloroacetimidate
  参考文献：
  名称：

  Total synthesis of 3-O-[2-acetamido-6-O-(N-acetyl-α-d-neuraminyl)-2-deoxy-α-d-galactosyl]-l-serine and a stereoisomer

  摘要：

  O-(5-Acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2- nonulopyranoxylonic acid)-(2----6)-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-(1----3) -L-serine, a structural unit occurring in various submaxillary mucins, was synthesized for the first time by using O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D- galacto-2-nonulopyranosyl)onate]-(2----6)-3,4-di-O-acetyl-2- azido-2-deoxy-D- galactopyranosyl trichloroacetimidate (13) and N-(benzyloxycarbonyl)-L-serine benzyl ester as the key intermediates. The trichloroacetimidate 13 was prepared by starting from two monosaccharide synthons, namely, allyl 2-azido-2-deoxy-beta-D-galactopyranoside and methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-beta-D- galacto-2-nonulopyranosyl chloride)onate, which were coupled in the presence of silver triflate in tetrahydrofuran to give the desired alpha-(2----6)-linked disaccharide in moderate selectivity.

  DOI：

  10.1016/s0008-6215(00)90853-x