phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-D-glucopyranoside | 439683-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R)-5-azido-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-ol
• CAS: 439683-95-1
• 化学式: C₂₆H₂₇N₃O₄S
• 分子量: 477.584
• InChiKey: IZWYBMSZWMSKHY-NCORMGPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-D-glucopyranoside 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 水 、 potassium carbonate 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 O-(4-O-Acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1,2-O-(L-1,7,7-trimethyl[2.2.1]bicyclohept-6-ylidene)-D-myo-inositol
  参考文献：
  名称：

  Inositolphosphoglycan Mediators Structurally Related to Glycosyl Phosphatidylinositol Anchors: Synthesis, Structure and Biological Activity

  摘要：

  The preparation of the pseudopentasaccharide 1a, an inositolphosphoglycan (IPG) that contains the conserved linear structure of glycosyl phosphatidylinositol anchors (GPI anchors), was carried out by using a highly convergent 2+3-block synthesis approach which involves imidate and sulfoxide glycosylation reactions. The preferred solution conformation of this structure was determined by using NMR spectroscopy and molecular dynamics simulations prior to carrying out quantitative structure-activity relationship studies in connection with the insulin signalling process. The ability of 1a to stimulate lipogenesis in rat adipocites as well as to inhibit cAMP dependent protein kinase and to activate pyruvate dehydrogenase phosphatase was investigated. Compound 1a did not show any significant activity, which may be taken as a strong indication that the GPI anchors are not the precursors of the IPG mediators.

  DOI：

  10.1002/1521-3765(20001002)6:19<3608::aid-chem3608>3.0.co;2-q
• 作为产物：
  描述：

  phenyl 2-azido-2-deoxy-1-thio-D-glucopyranoside 在 盐酸 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-D-glucopyranoside
  参考文献：
  名称：

  Inositolphosphoglycan Mediators Structurally Related to Glycosyl Phosphatidylinositol Anchors: Synthesis, Structure and Biological Activity

  摘要：

  The preparation of the pseudopentasaccharide 1a, an inositolphosphoglycan (IPG) that contains the conserved linear structure of glycosyl phosphatidylinositol anchors (GPI anchors), was carried out by using a highly convergent 2+3-block synthesis approach which involves imidate and sulfoxide glycosylation reactions. The preferred solution conformation of this structure was determined by using NMR spectroscopy and molecular dynamics simulations prior to carrying out quantitative structure-activity relationship studies in connection with the insulin signalling process. The ability of 1a to stimulate lipogenesis in rat adipocites as well as to inhibit cAMP dependent protein kinase and to activate pyruvate dehydrogenase phosphatase was investigated. Compound 1a did not show any significant activity, which may be taken as a strong indication that the GPI anchors are not the precursors of the IPG mediators.

  DOI：

  10.1002/1521-3765(20001002)6:19<3608::aid-chem3608>3.0.co;2-q

文献信息

• Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances
  作者：Jan Lindberg、Liselotte Öhberg、Per J Garegg、Peter Konradsson

  DOI：10.1016/s0040-4020(01)01241-8

  日期：2002.2

  Short synthetic routes to protected derivatives of 2-amino-2-deoxy-alpha-D-glucopyranosyl-(1-->6)-D-myo-inositol are described. Various 2-azido-2-deoxy-glucosyl donors were synthesized, starting front, D-Glucal or glucosamine hydrochloride. Derivatives of 1,2- and 2,3-D-myo-inositol-camphanylidene acetals were prepared to function as glycosyl acceptors. The subsequent glycosylations produced useful building blocks for the synthesis of GPI-anchor substances. (C) 2002 Elsevier Science Ltd. All rights reserved.
• [EN] PROCESS FOR THE PREPARATION OF POLYSACCHARIDES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE POLYSACCHARIDES
  申请人：UNIV MANCHESTER

  公开号：WO2014140626A3

  公开（公告）日：2014-11-06
• Inositolphosphoglycan Mediators Structurally Related to Glycosyl Phosphatidylinositol Anchors: Synthesis, Structure and Biological Activity
  作者：Manuel Martín-Lomas、Noureddine Khiar、Salud García、Jean-Luc Koessler、Pedro M. Nieto、Thomas W. Rademacher

  DOI：10.1002/1521-3765(20001002)6:19<3608::aid-chem3608>3.0.co;2-q

  日期：2000.10.2

  The preparation of the pseudopentasaccharide 1a, an inositolphosphoglycan (IPG) that contains the conserved linear structure of glycosyl phosphatidylinositol anchors (GPI anchors), was carried out by using a highly convergent 2+3-block synthesis approach which involves imidate and sulfoxide glycosylation reactions. The preferred solution conformation of this structure was determined by using NMR spectroscopy and molecular dynamics simulations prior to carrying out quantitative structure-activity relationship studies in connection with the insulin signalling process. The ability of 1a to stimulate lipogenesis in rat adipocites as well as to inhibit cAMP dependent protein kinase and to activate pyruvate dehydrogenase phosphatase was investigated. Compound 1a did not show any significant activity, which may be taken as a strong indication that the GPI anchors are not the precursors of the IPG mediators.