tert-butyldiphenylsilyl 2,4-diazido-2,4,6-trideoxy-β-D-glucopyranoside | 904891-28-7

• 分子结构分类: 有机化合物
• 英文名称: tert-butyldiphenylsilyl 2,4-diazido-2,4,6-trideoxy-β-D-glucopyranoside
• CAS: 904891-28-7
• 化学式: C₂₂H₂₈N₆O₃Si
• 分子量: 452.588
• InChiKey: YTAXEDDUULQXLW-WIGAVFHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  136.21
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyldiphenylsilyl 2,4-diazido-2,4,6-trideoxy-β-D-glucopyranoside 在 二氯二茂铪 、 4 A molecular sieve 、 sodium methylate 、 silver perchlorate 作用下， 以 甲醇 、 甲苯 、 苯 为溶剂， 反应 15.72h， 生成 tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-pentafluoropropionyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1->3)-2,4-diazido-2,4,6-trideoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of N-linked glycan derived from Gram-negative bacterium, Campylobacter jejuni

  摘要：

  Recent research has revealed the presence of asparagine (Asn)-linked (N-linked) glycoproteins in certain prokaryotes. In this paper, we describe the chemical synthesis of a novel N-glycan derived from Campylobacter jejuni, a heptasaccharide composed of Asn-linked bacillosamine (Bac), repeating GalNAc, and branching Glc, namely GalNAc-alpha(1,4)-GalNAc-alpha(1,4)-[Glc-beta(1,3)-] GalNAc-alpha(1,4)-GalNAc-alpha(1,4)-GalNAc-alpha(1,3)-Bac. The synthesis started from a Bac-acceptor, which was consecutively glycosylated with 4-O-pentafluoropropionyl (PFP) protected donors to give heptasaccharide. Reduction of azide groups was followed by debenzylation to complete the synthesis of the target oligosaccharide. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.126
• 作为产物：
  描述：

  tert-butyldiphenylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium azide 、 水 、 四丁基碘化铵 、 sodium hydride 、 sodium cyanoborohydride 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 二乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 153.5h， 生成 tert-butyldiphenylsilyl 2,4-diazido-2,4,6-trideoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of asparagine-linked bacillosamine

  摘要：

  Various types of protein glycosylation have been identified from prokaryotes. Recent investigations have revealed the presence of N-linked glycoproteins in the pathogenic bacterium, Campylobacter jejuni. The structure of this glycan is unique, consisting of 5 Ga1NAc and 1 G1c, in addition to 2,4-diacetamido-2,4,6-trideoxy-D-glucopyranose (bacillosamine; Bac), which is N-glycosidically linked to the side chain of asparagine (Asn). We synthesized Bac from a 2-azido-2-deoxy-D-galactose derivative, which was further converted to the Asn-linked form. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2006.04.031