ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide | 439684-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide
• 英文别名: (2S,3R,4R,5S,6R)-3-azido-2-ethylsulfinyl-4-phenylmethoxy-6-(phenylmethoxymethyl)-5-prop-2-enoxyoxane
• CAS: 439684-01-2
• 化学式: C₂₅H₃₁N₃O₅S
• 分子量: 485.604
• InChiKey: KCRLXZKXAYWXSX-MWHMNCAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  87.6
• 氢给体数：
  0
• 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 、 ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide 在 三氟甲磺酸酐 、 di-tert-butyl-methyl aminopyridine 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以63%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 2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 triflic azide 、 sodium hydride 、 sodium cyanoborohydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide
  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