Acetic acid (8R,10S)-10-acetoxymethyl-3,3-dimethyl-1,5,9-trioxa-spiro[5.5]undec-8-ylmethyl ester | 183952-46-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (8R,10S)-10-acetoxymethyl-3,3-dimethyl-1,5,9-trioxa-spiro[5.5]undec-8-ylmethyl ester
• 英文别名: [(8R,10S)-10-(acetyloxymethyl)-3,3-dimethyl-1,5,9-trioxaspiro[5.5]undecan-8-yl]methyl acetate
• CAS: 183952-46-7
• 化学式: C₁₆H₂₆O₇
• 分子量: 330.378
• InChiKey: UKDJPCFCEUTKGL-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (8R,10S)-10-acetoxymethyl-3,3-dimethyl-1,5,9-trioxa-spiro[5.5]undec-8-ylmethyl ester 在 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 、 Lipase PS 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 phosphate buffer 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 88.0h， 生成 2-hydroxymethyl-6-trityloxymethyl-tetrahydro-pyran-4-one
  参考文献：
  名称：

  Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

  摘要：

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.

  DOI：

  10.1021/ol015551o
• 作为产物：
  描述：

  5,5-dimethylspiro[1,3-dioxane-2,3'-8-oxabicyclo[3.2.1]oct-6-ene] 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 Acetic acid (8R,10S)-10-acetoxymethyl-3,3-dimethyl-1,5,9-trioxa-spiro[5.5]undec-8-ylmethyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

  摘要：

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.

  DOI：

  10.1021/ol015551o

文献信息

• Lipase mediated desymmetrization of meso-2,6-di(acetoxymethyl)-tetrahydropyran-4-one derivatives. An innovative route to enantiopure 2,4,6-trifunctionalized C-glycosides
  作者：Thomas F.J. Lampe、H.M.R. Hoffmann、Uwe T. Bornscheuer

  DOI：10.1016/0957-4166(96)00380-1

  日期：1996.10

  The desymmetrization of several meso-configurated 2,4,6-trifunctionalized tetrahydropyrans was studied. Amongst the derivatives investigated the conformationally more rigid spiro ketal 8b afforded hydroxy-acetate (-)-12 in excellent chemical yield and enantiomeric excess. The absolute configuration of the resulting 2,4,6-trifunctionalized C-glycosides was established by X-ray crystal diffraction. Copyright (C) 1996 Elsevier Science Ltd