(7E)-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 | 1236033-83-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (7E)-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
• CAS: 1236033-83-2
• 化学式: C₂₄H₃₇IN₂O₁₁
• 分子量: 656.469
• InChiKey: RCQBKQOMESFULZ-CPQGIFAJSA-N

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-1,2-乙二胺 、 (E/Z)-1,3,4,5-tetra-O-acetyl-2,6-anhydro-7,8,9-trideoxy-8,9-diiodo-L-glycero-D-allo-non-7-enitol 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以0.443 g的产率得到(7E)-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
  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