(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 | 114661-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (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
• 中文别名: 2-乙酰氨基-6-O-(Α-2-N-乙酰神经氨酰基)-2-脱氧-Α-D-吡喃半乳糖基丝氨酸
• 英文名称: O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine
• 英文别名: O-[N-acetyl-alpha-neuraminyl-(2->6)-N-acetyl-alpha-D-galactosaminyl]-L-serine；(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[(2S)-2-amino-2-carboxyethoxy]-3,4-dihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 114661-01-7
• 化学式: C₂₂H₃₇N₃O₁₆
• 分子量: 599.546
• InChiKey: RMINQIRDFIBNLE-NNRWGFCXSA-N

物化性质

• 熔点：
  188°C
• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -8.7
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  317
• 氢给体数：
  11
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 palladium on activated charcoal 、 Lindlar's catalyst sodium hydroxide 、 molecular sives 4A 、 molecular sives AW 、 氢气 、 sodium acetate 、 silver trifluoromethanesulfonate 、 potassium carbonate 、 TMSOTf 、 palladium dichloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 71.67h， 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

文献信息

• Total synthesis of 3-O-[2-acetamido-6-O-(N-acetyl-α-d-neuraminyl)-2-deoxy-α-d-galactosyl]-l-serine and a stereoisomer
  作者：Hiroyuki Iijima、Tomoya Ogawa

  DOI：10.1016/s0008-6215(00)90853-x

  日期：1988.2

  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.