1-(6-O-Acetyl-2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol | 158215-56-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(6-O-Acetyl-2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol
• 英文别名: [(2R,3S,4R,5R,6R)-5-azido-3,4-bis(phenylmethoxy)-6-[(1S,2R,3S,4R,5S,6R)-2,3,4,5-tetrakis(phenylmethoxy)-6-prop-2-enoxycyclohexyl]oxyoxan-2-yl]methyl acetate
• CAS: 158215-56-6
• 化学式: C₅₉H₆₃N₃O₁₁
• 分子量: 990.163
• InChiKey: IRIJNPMSCUMWDM-RQMLEPJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  73
• 可旋转键数：
  27
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1-(6-O-Acetyl-2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol 在 (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate 水 、 氢气 、 碘 作用下， 生成 1-(6-O-Acetyl-2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol
  参考文献：
  名称：

  An Effective Strategy for the Synthesis of 6-O-(2-Amino-2-deoxy-.alpha.-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-Phosphate Related to Putative Insulin Mimetics

  摘要：

  Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

  DOI：

  10.1021/jo00090a035
• 作为产物：
  描述：

  1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol 在 4-二甲氨基吡啶 、 3 A molecular sieve 、 四丁基溴化铵 、 乙酸酐 、 二正丁基氧化锡 、 TMSOTf 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 12.5h， 生成 1-(6-O-Acetyl-2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol
  参考文献：
  名称：

  An Effective Strategy for the Synthesis of 6-O-(2-Amino-2-deoxy-.alpha.-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-Phosphate Related to Putative Insulin Mimetics

  摘要：

  Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

  DOI：

  10.1021/jo00090a035