(2R,3R,4R,5S,6R)-2-Allyloxy-3,4,5-tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexanone | 135131-60-1

• 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: (2R,3R,4R,5S,6R)-2-Allyloxy-3,4,5-tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexanone
• CAS: 135131-60-1
• 化学式: C₃₈H₄₀O₇
• 分子量: 608.731
• InChiKey: NPJFAGQKUIJRNH-LOFFRUMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  45.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  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 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 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
• 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 、 3 A molecular sieve 、 三氟化硼乙醚 、 四丁基溴化铵 、 sodium hydride 、 二正丁基氧化锡 、 甲基磺酰氯 、 间氯过氧苯甲酸 、 三苯基膦 、 pyridinium chlorochromate 、 mercury dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 95.17h， 生成 (2R,3R,4R,5S,6R)-2-Allyloxy-3,4,5-tris-benzyloxy-6-(4-methoxy-benzyloxy)-cyclohexanone
  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。