(3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-bromo-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester | 132294-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-bromo-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS: 132294-62-3
• 化学式: C₅₂H₅₂BrNO₈S
• 分子量: 930.957
• InChiKey: OPFOOZIOQBUUAP-KAIMIFOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.86
• 重原子数：
  63.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  101.55
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-bromo-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester 在 palladium hydroxide - carbon 偶氮二异丁腈 、 mercury salt 、 三苯基氢化锡 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 重水 、 苯 为溶剂， 反应 581.0h， 生成 beta-D-Galactopyranoside, 4-methoxyphenyl 3-O-(N-acetyl-alpha-neuraminosyl)-
  参考文献：
  名称：

  Synthesis of human M blood group antigenic glycopeptide

  摘要：

  A first total synthesis of N-terminal glycoheptapeptide of human glycophorin AM was accomplished by solution phase peptide condensation utilizing the tetrasaccharide-linked amino acid building blocks designed for Fmoc strategy.

  DOI：

  10.1016/s0040-4039(00)76897-3

文献信息

• Stereoselective total synthesis of glycopeptides bearing the dimeric and trimeric sialosyl-Tn epitope
  作者：Yoshiaki Nakahara、Hiroyuki Iijima、Shohei Shibayama、Tomoya Ogawa

  DOI：10.1016/0008-6215(92)84163-m

  日期：1992.9

  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.
• Synthesis of the N-terminal glycopentapeptides of human glycophorin am and an carrying trimeric sialosyl Tn epitope
  作者：Hiroyuki Iijima、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0040-4039(00)74775-7

  日期：1992.12

  Pentapeptides with a cluster of sialosyl Tn epitopes, designed as models for MN blood group antigenic determinants of human glycophorin A, were synthesized in a stereocontrolled manner.