O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(benzyloxycarbonyl)-L-serine benzyl ester | 116246-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(benzyloxycarbonyl)-L-serine benzyl ester
• CAS: 116246-54-9；116299-45-7
• 化学式: C₅₀H₆₃N₃O₂₄
• 分子量: 1090.06
• InChiKey: OKZUUABMDDEZKI-OSWZWQKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  77.0
• 可旋转键数：
  24.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  343.85
• 氢给体数：
  3.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(benzyloxycarbonyl)-L-serine benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以15 mg的产率得到(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R,6S)-3,4-diacetoxy-5-acetylamino-6-((S)-2-amino-2-carboxy-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  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：

  O--(2->6)-3,4-di-O-acetyl-2-azido-2-deoxy-D-galactopyranose trichloroacetimidate 在 Lindlar's catalyst 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 19.17h， 生成 O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(benzyloxycarbonyl)-L-serine benzyl ester
  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