2-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-malonic acid diethyl ester | 192753-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-malonic acid diethyl ester
• CAS: 192753-12-1
• 化学式: C₃₄H₄₀O₉
• 分子量: 592.686
• InChiKey: WIYYQAOFGRYRSP-UPNJXQDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-malonic acid diethyl ester 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 、 水 、 溶剂黄146 、 叔丁醇 为溶剂， 反应 15.42h， 生成 (2S,3R,4R,5S,6R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-ethyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Synthesis and inhibitory effect of a trisubstrate transition state analogue for UDP glucuronosyltransferases

  摘要：

  Trisubstrate UGT transition state analogue 2 is readily accessible by nucleophilic ring-opening of 1,2-anhydroglucose precursor 5 with diethylmalonate anion followed by reduction of the ethyl ester moieties (6-->7). Subsequent C-6 oxidation (8-->9), NIS/cat. TfOH-mediated introduction of the androsterylmethylene unit (12-->15) and phosphitylation with 5'-uridine phosphoramidite 16 furnished, after oxidation and deprotection, target derivative 2, the two individual diastereomers of which (2a and 2b) were separated by HPLC. Trisubstrate analogues 2a,b show a different inhibition pattern for several UGT isoforms, indicating isoenzyme selectivity. Moreover, C-7-epimers 2a and 2b exert a different inhibitory effect on UGT2B15. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00251-5
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-D-glucal epoxide 、 丙二酸二乙酯 在 sodium hydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以76%的产率得到2-((2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-malonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and inhibitory effect of a trisubstrate transition state analogue for UDP glucuronosyltransferases

  摘要：

  Trisubstrate UGT transition state analogue 2 is readily accessible by nucleophilic ring-opening of 1,2-anhydroglucose precursor 5 with diethylmalonate anion followed by reduction of the ethyl ester moieties (6-->7). Subsequent C-6 oxidation (8-->9), NIS/cat. TfOH-mediated introduction of the androsterylmethylene unit (12-->15) and phosphitylation with 5'-uridine phosphoramidite 16 furnished, after oxidation and deprotection, target derivative 2, the two individual diastereomers of which (2a and 2b) were separated by HPLC. Trisubstrate analogues 2a,b show a different inhibition pattern for several UGT isoforms, indicating isoenzyme selectivity. Moreover, C-7-epimers 2a and 2b exert a different inhibitory effect on UGT2B15. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00251-5