benzyl 5-acetamido-2,7-anhydro-4,8,9-tri-O-benzyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-D-gluco-2-nonulopyranosonate | 136831-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 5-acetamido-2,7-anhydro-4,8,9-tri-O-benzyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-D-gluco-2-nonulopyranosonate
• CAS: 136831-30-6
• 化学式: C₄₅H₄₅NO₈S
• 分子量: 759.92
• InChiKey: AKYRCFZXWCDABT-FKBDHBEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  55.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101.55
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester 、 (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 4 A molecular sieve 、 氰化汞 、 mercury dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以41 mg的产率得到benzyl 5-acetamido-2,7-anhydro-4,8,9-tri-O-benzyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-D-gluco-2-nonulopyranosonate
  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