allyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(4-methoxybenzyl)-α-D-glucopyranoside | 1215016-47-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(4-methoxybenzyl)-α-D-glucopyranoside
• CAS: 1215016-47-9
• 化学式: C₃₁H₃₅N₃O₆
• 分子量: 545.635
• InChiKey: JDOKYVSAUQDZRJ-CWMPKMHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  40.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  104.14
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  allyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(4-methoxybenzyl)-α-D-glucopyranoside 在 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以80%的产率得到2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α/β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of a β-GlcN-(1→4)-MurNAc building block en route to N-deacetylated peptidoglycan fragments

  摘要：

  Some bacteria present a variation in their peptidoglycan structure that is the absence of the N-acetyl substituent in the glucosamine residue. Very recently, this structural modification was demonstrated to be critical for host innate immune evasion in Listeria monocytogenes. To shed light on the molecular details of the evasion mechanism, the synthesis of some N-deacetylated peptidoglycan fragments is needed. En route to this goal a high-yielding synthesis of a GlcN-MurNAc disaccharide building block has been accomplished. A careful study of the optimal protecting groups and reaction conditions was done to have a complete beta-stereoselectivity in glycosylation as well as to ensure a high versatility to the disaccharide building block. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.124
• 作为产物：
  描述：

  4-甲氧基苄醇 在 bismuth(lll) trifluoromethanesulfonate 、 sodium hydride 作用下， 以 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 26.0h， 生成 allyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(4-methoxybenzyl)-α-D-glucopyranoside
  参考文献：
  名称：

  p-Methoxybenzyl-N-phenyl-2,2,2-trifluoroacetimidate: a versatile reagent for mild acid catalyzed etherification

  摘要：

  PMB-NPTFA la is a new month bench stable and powerful reagent for the formation of PMB ethers. Several alcohols were protected in high yields and short reaction times, using low reagent loading and small catalytic amounts of Bi(OTf)(3). The mild conditions of the reaction confer a good orthogonality to acid- and base-sensitive protecting groups. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.066