p-toluenyl 4,6-O-benzylidene-2-O-levulinoyl-3-O-(2-naphthylmethyl)-L-thio-β-D-glucopyranoside | 1169693-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-toluenyl 4,6-O-benzylidene-2-O-levulinoyl-3-O-(2-naphthylmethyl)-L-thio-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7R,8S,8aR)-6-(4-methylphenyl)sulfanyl-8-(naphthalen-2-ylmethoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] 4-oxopentanoate
• CAS: 1169693-48-4
• 化学式: C₃₆H₃₆O₇S
• 分子量: 612.744
• InChiKey: YZXPOTYWIUGZQN-BMUWIQCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-toluenyl 4,6-O-benzylidene-2-O-levulinoyl-3-O-(2-naphthylmethyl)-L-thio-β-D-glucopyranoside 、 3,6-di-O-benzyl-1-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranose 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以85%的产率得到tert-butyldimethylsilyl 4,6-O-benzylidene-2-O-levulinoyl-3-O-(2-naphthylmethyl)-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a core trisaccharide building block for the assembly of N-glycan neoconjugates

  摘要：

  A short and high yielding synthesis of a core trisaccharide 1 as the key building block in the assembly of a library of N-glycan neoconjugates is presented. The beta-D-Manp-(1 -> 4)-D-GlcpNAc linkage was introduced by inversion of the C-2 position of a beta-glucoside. The glucosyl donor was efficiently synthesised following a recently published one-pot strategy. 2-Naphthylmethyl and benzylidene-acetal protection in the terminal mannose permitted selective liberation of main branching sites for subsequent glycosylation. A C5 azido linker attached to the anomeric position, which is stable throughout the synthesis, will allow for the posterior immobilisation of deprotected glycans on a microarray surface. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.028
• 作为产物：
  描述：

  p-tolyl 4,6-O-benzylidene-3-O-(naphthalene-2-ylmethyl)-1-thio-β-D-glucopyranoside 、 乙酰丙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到p-toluenyl 4,6-O-benzylidene-2-O-levulinoyl-3-O-(2-naphthylmethyl)-L-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a core trisaccharide building block for the assembly of N-glycan neoconjugates

  摘要：

  A short and high yielding synthesis of a core trisaccharide 1 as the key building block in the assembly of a library of N-glycan neoconjugates is presented. The beta-D-Manp-(1 -> 4)-D-GlcpNAc linkage was introduced by inversion of the C-2 position of a beta-glucoside. The glucosyl donor was efficiently synthesised following a recently published one-pot strategy. 2-Naphthylmethyl and benzylidene-acetal protection in the terminal mannose permitted selective liberation of main branching sites for subsequent glycosylation. A C5 azido linker attached to the anomeric position, which is stable throughout the synthesis, will allow for the posterior immobilisation of deprotected glycans on a microarray surface. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.028

文献信息

• Synthesis of a core trisaccharide building block for the assembly of N-glycan neoconjugates
  作者：Sonia Serna、Bharat Kardak、Niels-Christian Reichardt、Manuel Martin-Lomas

  DOI：10.1016/j.tetasy.2009.02.028

  日期：2009.5

  A short and high yielding synthesis of a core trisaccharide 1 as the key building block in the assembly of a library of N-glycan neoconjugates is presented. The beta-D-Manp-(1 -> 4)-D-GlcpNAc linkage was introduced by inversion of the C-2 position of a beta-glucoside. The glucosyl donor was efficiently synthesised following a recently published one-pot strategy. 2-Naphthylmethyl and benzylidene-acetal protection in the terminal mannose permitted selective liberation of main branching sites for subsequent glycosylation. A C5 azido linker attached to the anomeric position, which is stable throughout the synthesis, will allow for the posterior immobilisation of deprotected glycans on a microarray surface. (C) 2009 Elsevier Ltd. All rights reserved.