(R)-3-[(R)-2,2-dimethyl[1,3]dioxolan-4-yl]-2,2-dimethyl-3-(trimethylsilanyloxy)propionic acid methyl ester | 104602-05-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-3-[(R)-2,2-dimethyl[1,3]dioxolan-4-yl]-2,2-dimethyl-3-(trimethylsilanyloxy)propionic acid methyl ester
• 英文别名: (R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-3-trimethylsilanyloxypropionic acid methyl ester；(3R,4R)-2,2-Dimethyl-4,5-(isopropylidendioxy)-3-(trimethylsiloxy)pentansaeure-methylester；methyl (3R)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3-trimethylsilyloxypropanoate
• CAS: 104602-05-3
• 化学式: C₁₄H₂₈O₅Si
• 分子量: 304.459
• InChiKey: AVPXXZUUDSREML-MNOVXSKESA-N

物化性质

• 沸点：
  102-103 °C(Press: 1.5 Torr)
• 密度：
  0.994±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-[(R)-2,2-dimethyl[1,3]dioxolan-4-yl]-2,2-dimethyl-3-(trimethylsilanyloxy)propionic acid methyl ester 生成 [(2R,3R)-3-acetyloxy-4,4-dimethyl-5-oxooxolan-2-yl]methyl acetate
  参考文献：
  名称：

  KITA, YASUYUKI;TAMURA, OSAMU;ITOH, FUMIO;YASUDA, HITOSHI;KISHINO, HIROKO;+, J. ORG. CHEM., 53,(1988) N 3, 554-561

  摘要：

  DOI：
• 作为产物：
  描述：

  异丁酸甲酯 在 zinc(II) iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 2.0h， 生成 (R)-3-[(R)-2,2-dimethyl[1,3]dioxolan-4-yl]-2,2-dimethyl-3-(trimethylsilanyloxy)propionic acid methyl ester
  参考文献：
  名称：

  Pestalotiopsin A. Enantioselective Construction of Potential Building Blocks Derived from Antipodal Cyclobutanol Intermediates

  摘要：

  [GRAPHICS]D-Glyceraldehyde acetonide has been used as the starting point for accessing the enantiomeric cyclobutanols 11 in optically pure condition. The dextrorotatory enantiomer has been transformed in five steps into the [3.2.0] bicyclic lactone 22. While the deoxygenation of 22 proved to be problematical, the uncyclized variant 25 underwent the Barton process smoothly. These findings guided the related conversion of (-)-11 into 34. Use was also made of ring-closing metathesis to bring about the conversion of (+)-11 into [4.2.0] bicyclic lactone building blocks. In general, all three pathways are efficient and offer the prospect of practical side-chain appendage for the purpose of installing the nine-membered ring of pestalotiopsin A (1).

  DOI：

  10.1021/jo070861r

文献信息

• The chemistry of O-silylated ketene acetals; diastereoselective Aldol reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes leading to 2-deoxy-D (and L)-riboses
  作者：Yasuyuki Kita、Hitoshi Yasuda、Osamu Tamura、Fumio Itoh、Yuan Ke Ya、Yasumitsu Tamura

  DOI：10.1016/s0040-4039(00)98924-x

  日期：——

  Diastereoselective carbon-carbon bond forming reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes (D and L-2) with ketene silyl acetals (1a,b) occurred in acetonitrile under mild conditions to give the corresponding anti-β-siloxyesters (D and L-3a) as major products, which could be converted through a few additional steps to 2-deoxy-D(and L)-riboses.

  2,3-O-异亚丙基-D（和L）-甘油醛（D和L-2）与乙烯酮甲硅烷基缩醛（1a，b）的非对映选择性碳-碳键形成反应在温和的乙腈中发生，得到相应的抗-β-甲硅烷氧基酯（D和L-3a）为主要产物，可以通过一些额外的步骤将其转化为2-脱氧-D（和L）-核糖。
• Ipaktschi, Junes; Heydari, Akbar, Chemische Berichte, 1993, vol. 126, # 8, p. 1905 - 1912
  作者：Ipaktschi, Junes、Heydari, Akbar

  DOI：——

  日期：——
• KITA, YASUYUKI;TAMURA, OSAMU;ITOH, FUMIO;YASUDA, HITOSHI;KISHINO, HIROKO;+, J. ORG. CHEM., 53,(1988) N 3, 554-561
  作者：KITA, YASUYUKI、TAMURA, OSAMU、ITOH, FUMIO、YASUDA, HITOSHI、KISHINO, HIROKO、+

  DOI：——

  日期：——
• Pestalotiopsin A. Enantioselective Construction of Potential Building Blocks Derived from Antipodal Cyclobutanol Intermediates
  作者：Leo A. Paquette、Gregory D. Parker、Takahiro Tei、Shuzhi Dong

  DOI：10.1021/jo070861r

  日期：2007.9.1

  [GRAPHICS]D-Glyceraldehyde acetonide has been used as the starting point for accessing the enantiomeric cyclobutanols 11 in optically pure condition. The dextrorotatory enantiomer has been transformed in five steps into the [3.2.0] bicyclic lactone 22. While the deoxygenation of 22 proved to be problematical, the uncyclized variant 25 underwent the Barton process smoothly. These findings guided the related conversion of (-)-11 into 34. Use was also made of ring-closing metathesis to bring about the conversion of (+)-11 into [4.2.0] bicyclic lactone building blocks. In general, all three pathways are efficient and offer the prospect of practical side-chain appendage for the purpose of installing the nine-membered ring of pestalotiopsin A (1).