1,3,4,5-tetra-O-acetyl-2,6-anhydro-9-{[2-((tert-butyloxycarbonyl)amino)ethyl]amino}-7,8,9-trideoxy-L-glycero-D-allo-nonitol | 1236033-84-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,5-tetra-O-acetyl-2,6-anhydro-9-{[2-((tert-butyloxycarbonyl)amino)ethyl]amino}-7,8,9-trideoxy-L-glycero-D-allo-nonitol
• CAS: 1236033-84-3
• 化学式: C₂₄H₄₀N₂O₁₁
• 分子量: 532.588
• InChiKey: YCEHNEOOWRPNPK-LILSUDLASA-N

反应信息

• 作为反应物：
  描述：

  1,3,4,5-tetra-O-acetyl-2,6-anhydro-9-{[2-((tert-butyloxycarbonyl)amino)ethyl]amino}-7,8,9-trideoxy-L-glycero-D-allo-nonitol 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以90%的产率得到9-[(2-aminoethyl)amino]-2,6-anhydro-7,8,9-trideoxy-L-glycero-D-allo-nonitol dihydrochloride
  参考文献：
  名称：

  Synthesis of a C-galactopyranosyl-linked N-substituted 1,2-ethylenediamine

  摘要：

  A straightforward route to a C-galactopyranosyl-linked 1,2-ethylenediamine is described. The five-step synthetic procedure involves: (i) C-allenylation of D-galactopyranose pentaacetate with propargyl trimethylsilane in the presence of a Lewis acid, (ii) iodination of allenyl galactopyranosyl tetraacetate to diiodoallyl galactopyranosyl tetraacetate, (iii) displacement of the allylic iodide with N-Boc-ethylenediamine, (iv) catalytic hydrogenation of vinyl iodide to alkane, (v) deprotection of the acetyl and N-Boc-groups using acid-catalyzed hydrolysis. This method demonstrates a general method to access a new class of carbohydrate-ethylenediamine C-glycosyl chelators. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.03.040
• 作为产物：
  描述：

  1,3,4,5-tetra-O-acetyl-2,6-anhydro-9-{[2-((tert-butyloxycarbonyl)amino)ethyl]amino}-7,8,9-trideoxy-8-iodo-L-glycero-D-allo-non-7-enitol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以94%的产率得到1,3,4,5-tetra-O-acetyl-2,6-anhydro-9-{[2-((tert-butyloxycarbonyl)amino)ethyl]amino}-7,8,9-trideoxy-L-glycero-D-allo-nonitol
  参考文献：
  名称：

  Synthesis of a C-galactopyranosyl-linked N-substituted 1,2-ethylenediamine

  摘要：

  A straightforward route to a C-galactopyranosyl-linked 1,2-ethylenediamine is described. The five-step synthetic procedure involves: (i) C-allenylation of D-galactopyranose pentaacetate with propargyl trimethylsilane in the presence of a Lewis acid, (ii) iodination of allenyl galactopyranosyl tetraacetate to diiodoallyl galactopyranosyl tetraacetate, (iii) displacement of the allylic iodide with N-Boc-ethylenediamine, (iv) catalytic hydrogenation of vinyl iodide to alkane, (v) deprotection of the acetyl and N-Boc-groups using acid-catalyzed hydrolysis. This method demonstrates a general method to access a new class of carbohydrate-ethylenediamine C-glycosyl chelators. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.03.040