(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[(2S)-3-[[(2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-1-[[(1S)-1-carboxy-2-methylpropyl]amino]-1-oxopropan-2-yl]amino]-2-amino-3-oxopropoxy]-3,4-dihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid | 132209-51-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[(2S)-3-[[(2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-1-[[(1S)-1-carboxy-2-methylpropyl]amino]-1-oxopropan-2-yl]amino]-2-amino-3-oxopropoxy]-3,4-dihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 132209-51-9
• 化学式: C₄₉H₈₁N₇O₃₂
• 分子量: 1280.21
• InChiKey: FRBGADFAYRVTSB-YGWHVJRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.9
• 重原子数：
  88
• 可旋转键数：
  30
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  629
• 氢给体数：
  22
• 氢受体数：
  33

反应信息

• 作为产物：
  描述：

  在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 120.0h， 生成 (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[(2S)-3-[[(2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-6-[[(2R,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-1-[[(1S)-1-carboxy-2-methylpropyl]amino]-1-oxopropan-2-yl]amino]-2-amino-3-oxopropoxy]-3,4-dihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  Stereoselective total synthesis of glycopeptides bearing the dimeric and trimeric sialosyl-Tn epitope

  摘要：

  The dimeric and trimeric sialosyl-Tn epitopes, [alpha-D-Neup5Ac-(2----6)-alpha-D-GalpNAc-(1----3)-L-Ser]n-L-Val (n = 2 and 3), which represent part of a clustered carbohydrate region of glycophorin A, a human erythrocyte glycoprotein, have been synthesised stereoselectively. 2-Azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-galactopyranosyl fluoride (GalpNAc unit), Fmoc-L-serine phenacyl ester (Ser unit), and benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L - gluco-2-nonulopyranosylonate bromide (Neup5Ac unit) were the key intermediates for stereoselective glycosylation. 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline-promoted elongation of the peptide chain and then hydrogenolysis afforded the title compounds.

  DOI：

  10.1016/0008-6215(92)84163-m

文献信息

• YOSHIAKI, NAKAHARA;HIROYUKI, IIJIMA;SHOHEI, SIBAYAMA;OGAWA, TOMOYA, TETRAHEDRON LETT., 31,(1990) N7, C. 6897-6900
  作者：YOSHIAKI, NAKAHARA、HIROYUKI, IIJIMA、SHOHEI, SIBAYAMA、OGAWA, TOMOYA

  DOI：——

  日期：——