[(2R,3S,7S)-7-[tert-butyl(dimethyl)silyl]oxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate | 138381-66-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [(2R,3S,7S)-7-[tert-butyl(dimethyl)silyl]oxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate
• CAS: 138381-66-5
• 化学式: C₁₇H₃₀O₄Si
• 分子量: 326.508
• InChiKey: DCJSEXUBWCNWFT-UXLLHSPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2R,3S,7S)-7-[tert-butyl(dimethyl)silyl]oxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate 在 吡啶-N-氧化物 、 selenium(IV) oxide 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 Acetic acid (2R,3S,5S,7R)-7-(tert-butyl-dimethyl-silanyloxy)-5-fluoro-4-methylene-1-oxa-spiro[2.5]oct-2-ylmethyl ester
  参考文献：
  名称：

  Chemical conversion of vitamin D3 to its 1,35-dihydroxy metabolite

  摘要：

  Vitamin D3 (6) has been converted to the 1,25-dihydroxy vitamin D3 metabolite (1) and the 1-alpha-fluoro derivative 2 via a new process. The strategy involved the cleavage of the ring A portion from the CD portion in vitamin D3 followed by the individual modification of each subunit ot form 3, 4, and 5. The subsequent recombination of 3 and 5 formed 1 while 4 and 5 produced 2.

  DOI：

  10.1016/0040-4039(91)80752-r
• 作为产物：
  描述：

  乙酸乙烯酯 、 在 Candida antarctica lipase 作用下， 以 氯仿 为溶剂， 生成 [(2S,3R,7S)-7-[tert-butyl(dimethyl)silyl]oxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate 、 [(2R,3S,7S)-7-[tert-butyl(dimethyl)silyl]oxy-4-methylidene-1-oxaspiro[2.5]octan-2-yl]methyl acetate
  参考文献：
  名称：

  制备可完全合成1α，25-二羟基维生素D 3和与结构相关的同类物的A环构件：脂肪酶催化的合适环氧醇的立体选择性酯化

  摘要：

  对于维生素d的总合成中有用的A-环积木3个同类物，化合物7，已制备选自维生素d开始2通过依赖于脂肪酶催化酰化在用于立体选择性步骤的有机溶剂中的化学-酶促方法。

  DOI：

  10.1016/s0957-4166(00)00239-1

文献信息

• Chemical conversion of vitamin D3 to its 1,35-dihydroxy metabolite
  作者：Jaroslaw Kiegiel、Peter M. Wovkulich、Milan R. Uskoković

  DOI：10.1016/0040-4039(91)80752-r

  日期：1991.10

  Vitamin D3 (6) has been converted to the 1,25-dihydroxy vitamin D3 metabolite (1) and the 1-alpha-fluoro derivative 2 via a new process. The strategy involved the cleavage of the ring A portion from the CD portion in vitamin D3 followed by the individual modification of each subunit ot form 3, 4, and 5. The subsequent recombination of 3 and 5 formed 1 while 4 and 5 produced 2.
• Preparation of an A-ring building block for the total synthesis of 1α,25-dihydroxy vitamin D 3 and structurally related congeners: lipase-catalyzed stereoselective esterification of a suitable epoxyalcohol
  作者：Patrizia Ferraboschi、Shahrzad Reza-Elahi、Luca Scotti、Enzo Santaniello

  DOI：10.1016/s0957-4166(00)00239-1

  日期：2000.7

  An useful A-ring building block for the total synthesis of vitamin D3 congeners, compound 7, has been prepared starting from vitamin D2 by a chemo-enzymatic approach that relies on lipase-catalyzed acylation in an organic solvent for the stereoselective step.

  对于维生素d的总合成中有用的A-环积木3个同类物，化合物7，已制备选自维生素d开始2通过依赖于脂肪酶催化酰化在用于立体选择性步骤的有机溶剂中的化学-酶促方法。