2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol | 158215-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol
• 英文别名: [(2R,3S,4R,5R,6R)-5-azido-6-[(1R,2R,3R,4R,5R,6S)-2-bis(phenylmethoxy)phosphoryloxy-4,5,6-tris(phenylmethoxy)-3-prop-2-enoxycyclohexyl]oxy-3,4-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 158215-61-3
• 化学式: C₆₆H₇₀N₃O₁₄P
• 分子量: 1160.27
• InChiKey: XFLSXKPZQPYJQY-GSHJRISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  84
• 可旋转键数：
  32
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 在 (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate 氨 、 水 、 氢气 、 碘 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 70.08h， 生成 3,4,5-Tri-O-benzyl-1-O-(dibenzylphosphono)-6-(2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-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
• 作为产物：
  描述：

  (2R,3R,4R,5S,6R)-2-Allyloxy-3,4,5-tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexanone 在 ruthenium trichloride 四氮唑 、 sodium hydroxide 、 sodium periodate 、 R-Alpine-Hydride 、 双氧水 、 TMSOTf 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 11.5h， 生成 2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-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