pent-4-enyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 206353-04-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: pent-4-enyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6R)-5-azido-6-pent-4-enoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 206353-04-0
• 化学式: C₂₅H₃₁N₃O₅
• 分子量: 453.538
• InChiKey: GMFDGYQLGDQXDQ-FXEFVXDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 4-O-[4,6-O-benzylidene-2-O-benzyl-β-D-mannopyranosyl]-(1->4)-pent-4-enyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  1-Naphthylpropargyl Ether Group:  A Readily Cleaved and Sterically Minimal Protecting System for Stereoselective Glycosylation

  摘要：

  [GRAPHICS]The (1-naphthyl) propargyl group is introduced as a sterically unobtrusive alcohol protecting group that is cleaved in a single step by exposure to dichlorodicyanoquinone in wet dichloromethane. In conjunction with the 4,6-O-benzylidene protecting group, and the use of the sulfoxide glycosylation method, 3-O-naphthylpropargyl-protected mannosyl donors are extremely beta-selective.

  DOI：

  10.1021/ol061938l
• 作为产物：
  描述：

  pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 triflic azide 、 乙二胺 作用下， 生成 pent-4-enyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Tetrachlorophthalimido- and Pent-4-enoyl-Protected Glucosamines as Precursors for Preparation of 2-Azido-2-deoxyglucopyranosyl Building Blocks

  摘要：

  DOI：

  10.1021/jo980427c

文献信息

• A short synthesis of the trisaccharide building block of the N-linked glycans
  作者：Vadim Y. Dudkin、David Crich

  DOI：10.1016/s0040-4039(03)00102-3

  日期：2003.2

  An efficient preparation of the core trisaccharide of N-linked glycoproteins containing β-azido functionality at the reducing terminus is described. In the synthesis, triflate-mediated direct β-mannosylation was employed for the formation of the β-d-Man-(1→4)-GlcNAc linkage; the anomeric azide installation was achieved through oxazoline ring opening.

  描述了在还原末端含有β-叠氮基官能团的N-连接糖蛋白的核心三糖的有效制备。在合成中，使用三氟甲磺酸酯介导的直接β-甘露糖基化作用形成β-d-Man-（1→4）-GlcNAc键；异头叠氮化物的安装是通过恶唑啉开环实现的。
• 1-Naphthylpropargyl Ether Group:  A Readily Cleaved and Sterically Minimal Protecting System for Stereoselective Glycosylation
  作者：David Crich、Baolin Wu

  DOI：10.1021/ol061938l

  日期：2006.10.1

  [GRAPHICS]The (1-naphthyl) propargyl group is introduced as a sterically unobtrusive alcohol protecting group that is cleaved in a single step by exposure to dichlorodicyanoquinone in wet dichloromethane. In conjunction with the 4,6-O-benzylidene protecting group, and the use of the sulfoxide glycosylation method, 3-O-naphthylpropargyl-protected mannosyl donors are extremely beta-selective.
• Tetrachlorophthalimido- and Pent-4-enoyl-Protected Glucosamines as Precursors for Preparation of 2-Azido-2-deoxyglucopyranosyl Building Blocks
  作者：Lars Olsson、Zhaozhong J. Jia、Bert Fraser-Reid

  DOI：10.1021/jo980427c

  日期：1998.5.1