1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol | 135267-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol
• 英文别名: (1R,2S,3R,4S,5S,6S)-3,4,5-tris(phenylmethoxy)-6-prop-2-enoxycyclohexane-1,2-diol
• CAS: 135267-00-4
• 化学式: C₃₀H₃₄O₆
• 分子量: 490.596
• InChiKey: FCFCHTVNSSOGKC-YUCFEETJSA-N

物化性质

• 沸点：
  615.5±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 四碘甲烷 、 三氟化硼乙醚 、 sodium hydride 、 甲基磺酰氯 、 间氯过氧苯甲酸 、 三苯基膦 、 mercury dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.17h， 生成 1-O-Allyl-2,3,4-tri-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

文献信息

• Approaches to the synthesis of glycosyl phosphatidyl inositols. Enantioselective synthesis of optically active chiro- and myo-inositols.
  作者：Carlos Jaramillo、Manuel Martin-Lomas

  DOI：10.1016/s0040-4039(00)74366-8

  日期：1991.11

  substituted D-chiro (5 and D-myo-inositol (10 derivatives has been developed starting from methyl α-D-glucopyranoside. Compounds 5 and 10 constitute valuable intermediates for the preparation of glycosyl phosphatidyl inositols.

  一种有效的合成策略，以光学活性方便地取代的D-手性（5和D-肌肌醇（10个衍生物已被开发从甲基α-d-D-吡喃葡萄糖苷起始。化合物5和10构成用于糖基磷脂酰肌醇的制备有价值的中间体。