N-(9-fluorenylmethyloxycarbonyl)-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester | 125762-72-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(9-fluorenylmethyloxycarbonyl)-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester
• CAS: 125762-72-3
• 化学式: C₄₁H₄₄N₂O₁₄
• 分子量: 788.805
• InChiKey: KHBSZDFXTDANSO-XCGXIDLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  57.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  208.16
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  sodium methylate 、 N-(9-fluorenylmethyloxycarbonyl)-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester 以 甲醇 为溶剂， 反应 0.5h， 以72%的产率得到N-(9-fluorenylmethyloxycarbonyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine methylester
  参考文献：
  名称：

  Efficient Chemoenzymatic Synthesis of O-Linked Sialyl Oligosaccharides

  摘要：

  The tumor associated Tn (GalNAcalpha(1-1)-Thr/Ser)- and T (Galbeta(1-3)-GalNAcalpha(1-1)Thr/Ser)antigens and their sialylated derivatives are present on the surface of many cancer cells. Preparative synthesis of these sialylated T- and Tn-structures has been achieved mainly from a chemical synthetic approach due to the lack of the required glycosyltransferases. We demonstrate a flexible and efficient chemoenzymatic approach for using recombinant sialyltransferases including a chicken GalNAcalpha2,6-sialyltransferase (chST6GalNAc1) and a porcine Galbeta(1-3)GalNAcalpha-2,3-sialyltransferase (pST3Gal 1). Using these enzymes, the common O-linked sialosides Neu5Acalpha(2-6)GalNAcalpha(1-1)Thr, Galbeta(1-3)[Neu5Acalpha(26)]GalNAcalpha(1-1)Thr, Neu5Acalpha(2-3)Galbeta(1-3)GalNAcalpha(1-1)Thr, and Neu5Acalpha(2-3)Galbeta(1-3)[Neu5Acalpha(-26)]GalNAcalpha(1-1)Thr were readily prepared at preparative scale. The chST6GalNAc I was found to require at least one amino acid (Thr/Ser) for optimal activity, and is thus an ideal catalyst for synthesis of synthetic glycopeptides and glycoconjugates with O-linked glycans.

  DOI：

  10.1021/ja017881+
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl)-L-threonine phenacyl ester 、 硫代乙酸 以55%的产率得到N-(9-fluorenylmethyloxycarbonyl)-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester
  参考文献：
  名称：

  Synthesis of TN and T Antigen Glycopeptide Sequences of tumor-associated MUC-1 usingS-pent-4-enyl thioglycosides

  摘要：

  The syntheses of glycopeptides 34 and 38 with tumor associated T-N and T antigen structure containing a partial sequence of the tandem repeat unit of the polymorphic epithelial mucin MUC-1 were achieved via fragment condensations. Electrophilic activation of S-pent-4-enyl thioglycosides was applied for the construction of O-glycosyl amino acid and saccharide building blocks.

  DOI：

  10.1002/prac.19973390160