O-(4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl) trichloroacetimidate | 201015-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl) trichloroacetimidate
• 英文别名: [(2S,3R,4R,5S,6R)-3-azido-4-phenylmethoxy-6-(phenylmethoxymethyl)-5-prop-2-enoxyoxan-2-yl] 2,2,2-trichloroethanimidate
• CAS: 201015-92-1
• 化学式: C₂₅H₂₇Cl₃N₄O₅
• 分子量: 569.872
• InChiKey: HAGWBPBIMORDBM-JLMDMGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  D-1,4,5-tri-O-trimethylacetyl-2,3-O-(D-1,7,7-trimethyl<2.2.1>bicyclohept-2-ylidene)-myo-inositol 、 O-(4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl) trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 为溶剂， 以43%的产率得到6-O-(4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1,4,5-tri-O-trimethylacetyl-2,3-O-(D-1,7,7-trimethyl[2.2.1]bicyclohept-6-ylidene)-D-myo-inositol
  参考文献：
  名称：

  Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)01241-8
• 作为产物：
  描述：

  ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 在 三氟甲磺酸 、 potassium carbonate 、 四丁基高碘酸铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 O-(4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl) trichloroacetimidate
  参考文献：
  名称：

  Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)01241-8