tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-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 | 949006-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-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
• 英文别名: (2R,3R,4R,5R,6R)-5-azido-6-[(2R,3R,4R,5R,6S)-5-azido-6-[(2S,3R,4S,5R,6R)-3,5-diazido-2-[tert-butyl(diphenyl)silyl]oxy-6-methyloxan-4-yl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 949006-18-2
• 化学式: C₆₂H₇₀N₁₂O₁₁Si
• 分子量: 1187.4
• InChiKey: VLAVVJWJSAGOEA-AJAJDTDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.21
• 重原子数：
  86
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-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 在 sodium tetrahydroborate 、 cobalt(II) chloride hexahydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation

  摘要：

  Synthesis of undecaprenyl pyrophosphate (Und-PP)-linked glycans is described. Bacterial ([E](3),[Z](7))-undecaprenol was synthesized from trans-geranylgeranyl sulfone and isoprenoid building blocks, which was converted to undecaprenyl phosphate (Und-P). It was coupled with glycosyl phosphates to afford Und-PP-linked glycans, including core trisaccharide of Campylobacter jejuni N-glycan. Our synthetic method for Und-PP-linked glycan would provide various substrates as a useful tool for systematic analysis of bacterial protein N-glycosylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.032
• 作为产物：
  描述：

  tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1->3)-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 7.72h， 生成 tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-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

文献信息

• Synthesis of N-linked glycan derived from Gram-negative bacterium, Campylobacter jejuni
  作者：Mohammed Nurul Amin、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1016/j.tet.2007.05.126

  日期：2007.8

  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.
• Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation
  作者：Yong Joo Lee、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1016/j.tet.2009.06.032

  日期：2009.8

  Synthesis of undecaprenyl pyrophosphate (Und-PP)-linked glycans is described. Bacterial ([E](3),[Z](7))-undecaprenol was synthesized from trans-geranylgeranyl sulfone and isoprenoid building blocks, which was converted to undecaprenyl phosphate (Und-P). It was coupled with glycosyl phosphates to afford Und-PP-linked glycans, including core trisaccharide of Campylobacter jejuni N-glycan. Our synthetic method for Und-PP-linked glycan would provide various substrates as a useful tool for systematic analysis of bacterial protein N-glycosylation. (C) 2009 Elsevier Ltd. All rights reserved.