2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-D-myo-inositol | 158215-60-2

• 英文名称: 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-D-myo-inositol
• 英文别名: dibenzyl [(1S,2R,3R,4S,5R,6R)-2-hydroxy-3,4,5-tris(phenylmethoxy)-6-prop-2-enoxycyclohexyl] phosphate
• CAS: 158215-60-2
• 化学式: C₄₄H₄₇O₉P
• 分子量: 750.826
• InChiKey: SHQAOAYTVWEFPU-DKSITQHISA-N

物化性质

• 沸点：
  818.3±65.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  54
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-D-myo-inositol 在 palladium on activated charcoal 、 (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate 氨 、 水 、 氢气 、 碘 、 TMSOTf 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， -20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 90.58h， 生成 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate
  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 ruthenium trichloride 四氮唑 、 sodium hydroxide 、 sodium periodate 、 R-Alpine-Hydride 、 3 A molecular sieve 、 四丁基溴化铵 、 双氧水 、 二正丁基氧化锡 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-D-myo-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