2-azido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl diphenyl phosphate | 608124-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl diphenyl phosphate
• 英文别名: 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl diphenyl phosphate；(2S,3R,4R,5S,6R)-3-azido-2-[oxido(diphenoxy)phosphaniumyl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 608124-97-6
• 化学式: C₃₉H₃₈N₃O₈P
• 分子量: 707.72
• InChiKey: ZMMOPIBSGHBSMH-GKFPOLJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 2-azido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl diphenyl phosphate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 methyl-2,3,6-tri-O-benzyl-4-O-(2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  A stereocontrolled construction of 2-azido-2-deoxy-1,2-trans-β-glycosidic linkages utilizing 2-azido-2-deoxyglycopyranosyl diphenyl phosphates

  摘要：

  A high-yielding and stereocontrolled construction of 2-azido-2-deoxy-1,2-trans-beta-glycosidic linkages has been achieved by exploiting TMSOTf-promoted 1,2-trans-glycosidation of 2-azido-2-deoxyglycopyranosyl diphenyl phosphates with various glycoside alcohols in propionitrile at -78degreesC. The present method exhibits the highest levels of 1,2-trans-beta-selectivity reported to date for this type of glycosidation. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01557-0
• 作为产物：
  描述：

  磷酸二苯酯 、 2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 以 二氯甲烷 为溶剂， 反应 0.1h， 以86%的产率得到2-azido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl diphenyl phosphate
  参考文献：
  名称：

  A highly stereoselective construction of 1,2-trans-β-glycosidic linkages capitalizing on 2-azido-2-deoxy-d-glycosyl diphenyl phosphates as glycosyl donors

  摘要：

  The scope of TMSOTf-promoted glycosidation of 2-azido-2-deoxyglycopyranosyl diphenyl phosphates is investigated. The 3,4,6-tri-O-benzyl-protected glucosyl and galactosyl donors and the 4,6-O-benzylidene-protected galactosyl donor each react with a range of acceptor alcohols in the presence of a stoichiometric amount of TMSOTf in propionitrile at -78 degreesC to afford 1,2-trans-beta-linked disaccharides in high yields with alpha:beta ratios ranging from 9:91 to 1: > 99, regardless of the anomeric composition of the donor used. The use of propionitrile as a solvent at -78 degreesC has proven to be among the best choice for the highest levels of beta-selectivity reported to date for this type of glycosidation. A plausible reaction mechanism, which features a large equilibrium preference for alpha-glycosyl-nitrilium ions over beta-nitrilium ions, is proposed based on byproducts formed through their intermediacy and accounts for the observed excellent beta-selectivities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.076