(2S,3S,4S,5R)-[4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-acetic acid methyl ester | 724733-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,3S,4S,5R)-[4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-acetic acid methyl ester
• 英文别名: methyl 2-[(2R,3S,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-6-oxooxan-2-yl]acetate
• CAS: 724733-38-4
• 化学式: C₁₆H₃₀O₅Si
• 分子量: 330.497
• InChiKey: KFVCFRCOUJPCLS-SFTQSGBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R)-[4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-acetic acid methyl ester 在 Pd-BaSO₄ 喹啉 、 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 16.0h， 生成 methyl 2-[(2R,3S,4S,5R,6S)-6-[(Z,4S,5S)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyhept-1-enyl]-4-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-3,5-dimethyloxan-2-yl]acetate
  参考文献：
  名称：

  Lactol-Directed Osmylation. Stereodivergent Synthesis of Four C-19,20 Apoptolidin Diols from a Single Allylic Hemiacetal

  摘要：

  A synthetic approach to prepare four Apoptolidin C-19,20 diastereomeric diol derivatives was developed. Two diastereomers were obtained from the (Z)-form, which is converted to the (E)-form, followed by dihydroxylation to deliver two more diastereomers. The (E)-allylic hemiacetal and methoxyacetal showed opposite diastereoselectivity.

  DOI：

  10.1021/ol0707564
• 作为产物：
  描述：

  (2R,3S,4S,5R)-[4-(tert-butyldimethylsilanyloxy)-6-hydroxy-3,5-dimethyltetrahydropyran-2-yl]-acetic acid methyl ester 在 ruthenium trichloride sodium bromate 、 phosphate buffer 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 6.0h， 以90%的产率得到(2S,3S,4S,5R)-[4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-6-oxotetrahydropyran-2-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Lactol-Directed Osmylation. Stereodivergent Synthesis of Four C-19,20 Apoptolidin Diols from a Single Allylic Hemiacetal

  摘要：

  A synthetic approach to prepare four Apoptolidin C-19,20 diastereomeric diol derivatives was developed. Two diastereomers were obtained from the (Z)-form, which is converted to the (E)-form, followed by dihydroxylation to deliver two more diastereomers. The (E)-allylic hemiacetal and methoxyacetal showed opposite diastereoselectivity.

  DOI：

  10.1021/ol0707564

文献信息

• Chemical synthons and intermediates
  申请人：——

  公开号：US20040138485A1

  公开（公告）日：2004-07-15

  The invention provides novel six and seven-carbon termini-differentiated polypropionate stereotetrads and stereopentads useful in syntheses of natural products. The invention also provides a novel alkylative sulfenylation-desulfonylation process that efficiently transforms enantiopure epoxyvinyl sulfones to syn and anti dienylsulfides in two operations.

  这项发明提供了新颖的六碳和七碳末端差异化的聚丙酸酯立体四聚体和立体五聚体，可用于合成天然产物。该发明还提供了一种新颖的烷基化磺化-去磺化过程，能够高效地将对映纯环氧乙烯基磺酮转化为syn和anti二烯基硫醚，只需两步操作。