benzyl 2-[(2R,3R,4S,5S,6R)-6-(azidomethyl)-5-hydroxy-2-methoxy-4-phenylmethoxyoxan-3-yl]oxyacetate | 1169754-34-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-[(2R,3R,4S,5S,6R)-6-(azidomethyl)-5-hydroxy-2-methoxy-4-phenylmethoxyoxan-3-yl]oxyacetate
• CAS: 1169754-34-0
• 化学式: C₂₃H₂₇N₃O₇
• 分子量: 457.483
• InChiKey: XOIYDNUNFAONRN-YDXQKAQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 、 benzyl 2-[(2R,3R,4S,5S,6R)-6-(azidomethyl)-5-hydroxy-2-methoxy-4-phenylmethoxyoxan-3-yl]oxyacetate 在 2,3,5-三甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 乙醚 、 甲苯 为溶剂， 以70%的产率得到methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->4)-3-O-benzyl-6-azido-2-benzyl-acetate-6-deoxy-β-D-galactopyranosyide
  参考文献：
  名称：

  A sugar aminoacid for the development of multivalent ligands for Escherichia coli 0157 verotoxin

  摘要：

  Functionalised carbohydrates for incorporation into multivalent ligands for the Escherichia coli O157 verotoxin are highly desirable. Here, we report the synthesis of a sugar aminoacid based on the known Gal-alpha-1,4-Gal ligand for verotoxin in eight steps and in similar to 10% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.021
• 作为产物：
  描述：

  、 溴甲苯 在 二正丁基氧化锡 、 四丁基溴化铵 作用下， 以 甲醇 、 甲苯 为溶剂， 以51%的产率得到benzyl 2-[(2R,3R,4S,5S,6R)-6-(azidomethyl)-5-hydroxy-2-methoxy-4-phenylmethoxyoxan-3-yl]oxyacetate
  参考文献：
  名称：

  A sugar aminoacid for the development of multivalent ligands for Escherichia coli 0157 verotoxin

  摘要：

  Functionalised carbohydrates for incorporation into multivalent ligands for the Escherichia coli O157 verotoxin are highly desirable. Here, we report the synthesis of a sugar aminoacid based on the known Gal-alpha-1,4-Gal ligand for verotoxin in eight steps and in similar to 10% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.021

文献信息

• A sugar aminoacid for the development of multivalent ligands for Escherichia coli 0157 verotoxin
  作者：Darren Gibson、Steven W. Homans、Robert A. Field

  DOI：10.1016/j.tetasy.2009.02.021

  日期：2009.5

  Functionalised carbohydrates for incorporation into multivalent ligands for the Escherichia coli O157 verotoxin are highly desirable. Here, we report the synthesis of a sugar aminoacid based on the known Gal-alpha-1,4-Gal ligand for verotoxin in eight steps and in similar to 10% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.