methyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-azido-2-deoxy-4,6-O-benzylidene-β-D-galactopyranoside | 191341-73-8

• 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: methyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-azido-2-deoxy-4,6-O-benzylidene-β-D-galactopyranoside
• 英文别名: methyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside；[(2R,3S,4S,5R,6R)-6-[[(2S,4aR,6R,7R,8R,8aR)-7-azido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 191341-73-8
• 化学式: C₂₈H₃₅N₃O₁₄
• 分子量: 637.598
• InChiKey: LCETXOLWJXKNOV-NCQKCXHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  175
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-azido-2-deoxy-4,6-O-benzylidene-β-D-galactopyranoside 在 吡啶 、 硫酸 、 溶剂黄146 作用下， 生成
  参考文献：
  名称：

  Chemoselectively template-assembled glycopeptide presenting clustered cancer related T-antigen

  摘要：

  The first synthesis of the tumor-associated alpha-aminooxy T-antigen 1, a relevant recognition motif for the direct construction of multitopic carbohydrate architecture of biological interest is described. The usefulness of this building block is emphasized with the efficient preparation through oxime ligation of a neoglycopeptide cluster, which is readily suitable for evaluating the role of multivalency in antigen presentation to the immune system from an anticancer vaccine perspective. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.126
• 作为产物：
  描述：

  methyl 2-azido-2-deoxy-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 生成 methyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-azido-2-deoxy-4,6-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Chemoselectively template-assembled glycopeptide presenting clustered cancer related T-antigen

  摘要：

  The first synthesis of the tumor-associated alpha-aminooxy T-antigen 1, a relevant recognition motif for the direct construction of multitopic carbohydrate architecture of biological interest is described. The usefulness of this building block is emphasized with the efficient preparation through oxime ligation of a neoglycopeptide cluster, which is readily suitable for evaluating the role of multivalency in antigen presentation to the immune system from an anticancer vaccine perspective. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.126

文献信息

• Synthesis of the glycosyl amino acids Nα-Fmoc-Ser[Ac4-β-d-Gal p-(1 → 3)-Ac2-α-d-GalN3 p]-OPfp and Nα-Fmoc-Thr[Ac4-β-d-Gal p-(1 → 3)-Ac2-α-d-GalN3 p]-OPfp and the application in the solid-phase peptide synthesis of multiply glycosylated mucin peptides with Tn and T antigenic structures
  作者：Hans Paulsen、Stefan Peters、Tim Bielfeldt、Morten Meldal、Klaus Bock

  DOI：10.1016/0008-6215(94)00292-n

  日期：1995.3

  -β- d -Gal p-(1 → 3)- Ac 2 -α- d -GalN 3 p]- OPfp and N α - Fmoc-Thr[Ac 4 -β- d -Gal p-(1 → 3)- Ac 2 -α- d -GalN 3 p]- OPfp were synthesized. Glycosylation of Nα-Fmoc-Ser-OPfp or Nα-Fmoc-Thr-OPfp with protected β- d -Gal -(1 → 3)- d -GalN 3 donors afforded the glycosyl amino acids containing an activated C-terminus which could be utilized directly for solid-phase glycopeptide synthesis. The transformation

  摘要两个新的糖基氨基酸Nα-Fmoc-Ser [Ac 4-β-d -Gal p-（1→3）-Ac 2-α-d -GalN 3 p]-OPfp和Nα-Fmoc-Thr [合成了Ac 4-β-d -Gal p-（1→3）-Ac 2-α-d -GalN 3 p] -OPfp。Nα-Fmoc-Ser-OPfp或Nα-Fmoc-Thr-OPfp的糖基化与受保护的β-d -Gal-（1→3）-d -GalN 3供体进行糖基化，得到的糖基氨基酸含有一个活化的C末端，可以是直接用于固相糖肽合成。在合成结束时，通过用硫代乙酸处理与聚合物结合的糖肽，可以定量实现2-叠氮基向乙酰氨基衍生物的转化。八种三糖基化粘蛋白肽的组装证明了该策略的多功能性，这些肽是通过多柱技术同时合成的。
• Synthesis of TN and T Antigen Glycopeptide Sequences of tumor-associated MUC-1 usingS-pent-4-enyl thioglycosides
  作者：Michael Leuck、Horst Kunz

  DOI：10.1002/prac.19973390160

  日期：——

  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.