(R)-3-hydroxy-O,O'-bis(trimethylsilyl)buttersaeure | 108438-96-6

• 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: (R)-3-hydroxy-O,O'-bis(trimethylsilyl)buttersaeure
• 英文别名: trimethylsilyl (R)-3-trimethylsiloxy butyrate；trimethylsilyl (R)-3-<(trimethylsilyl)oxy>butyrate；bis(TMS)-(3R)-3-hydroxybutyric acid；(3R)-3-hydroxybutyrylbis(TMS)；trimethylsilyl (3R)-3-trimethylsilyloxybutanoate
• CAS: 108438-96-6
• 化学式: C₁₀H₂₄O₃Si₂
• 分子量: 248.47
• InChiKey: YWRIHOYCAHATJN-SECBINFHSA-N

物化性质

• 沸点：
  220.5±23.0 °C(predicted)
• 密度：
  0.902±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxy-O,O'-bis(trimethylsilyl)buttersaeure 、 特戊醛 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到(2R,6R)-2-叔丁基-6-甲基-1,3-二噁烷-4-酮
  参考文献：
  名称：

  Optisch aktive Alkohole aus 1,3-Dioxan-4-onen：eine praktikable Variante der enantioselektiven合成亲核试剂取代乙缩醛†

  摘要：

  1,3-二恶烷-4-酮类的旋光醇。在乙缩醛中心的亲核取代对映选择性合成的实用版本。

  DOI：

  10.1002/hlca.19870700226
• 作为产物：
  描述：

  三甲基氯硅烷 、 (R)-3-羟基丁酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以94%的产率得到(R)-3-hydroxy-O,O'-bis(trimethylsilyl)buttersaeure
  参考文献：
  名称：

  Optisch aktive Alkohole aus 1,3-Dioxan-4-onen：eine praktikable Variante der enantioselektiven合成亲核试剂取代乙缩醛†

  摘要：

  1,3-二恶烷-4-酮类的旋光醇。在乙缩醛中心的亲核取代对映选择性合成的实用版本。

  DOI：

  10.1002/hlca.19870700226

文献信息

• A highly stereoselective synthesis of the 1β-methylcarbapenem key intermediate from (R)-3-hydroxybutyric acid
  作者：Yuko Kobayashi、Yoshio Ito、Shiro Terashima

  DOI：10.1016/s0040-4020(01)80578-0

  日期：1992.1

  Baeyer-Villiger reaction accompanying novel cleavage of the acetal moiety. The Reformatsky reaction of 6 with sterically crowded 3-(2-bromopropionyl)-2-oxazolidone derivatives readily afforded the title key intermediate after sequential chemical manipulations.

  （3R，4R）-4-乙酰氧基-3-[（R）-1-（甲酰氧基）乙基] -2-氮杂环丁酮6可以通过[2 + 2 ]从（R）-3-羟基丁酸高立体选择性地制备氯磺酰基异氰酸酯与2H，4H-1,3-二恶英衍生物的]-环加成反应和伴随乙缩醛部分新裂解的Baeyer-Villiger反应。6与空间拥挤的3-（2-溴丙酰基）-2-恶唑烷酮衍生物的Reformatsky反应在连续的化学操作后很容易提供标题关键中间体。
• On the preparation of optically active secondary alcohols from a 1,3-dioxan-4-one: Substitution with organocopper reagents
  作者：Stuart L. Schreiber、Jeff Reagan

  DOI：10.1016/s0040-4039(00)84686-9

  日期：——

  Organocopper reagents react with a chiral nonracemic 1,3-dioxan-4-one to afford substitution products with high diastereoselectivity. After treatment of the adducts with potassium t-butoxide, optically active secondary alcohols are obtained.

  有机铜试剂与手性非外消旋1,3-二恶烷-4-酮反应，可提供具有高非对映选择性的取代产物。用叔丁醇钾处理加合物后，获得旋光性仲醇。
• Bromination of 2,2,6-trialkyl-1,3-dioxan-4-ones. Application of the deuterium isotope effect to the synthesis of a chiral trialkyldioxinone
  作者：Gordon L. Lange、Michael G. Organ、Michael R. Roche

  DOI：10.1021/jo00048a039

  日期：1992.10

  Free-radical bromination (2 equiv of NBS) of 2-tert-butyl-2,6-dimethyl-1,3-dioxan-4-one (6a) gives the 2-bromomethyl product 7a. By contrast, bromination of 2-tert-butyl-2-methyl-1,3-dioxan-4-one (1) is reported to occur at the 6-position. Deuterium-labeling experiments established that 7a is formed by direct substitution at the 2-methyl group of 6a and not by abstraction of H-6 followed by hydrogen atom transfer from the 2-methyl group and bromination of the resultant primary radical 12. When 2-tert-butyl-6-methyl-2-(methyl-d3)-1,3-dioxan-4-one (13) is reacted with 4 equiv of NBS, the course of the reaction is altered dramatically and the major product formed in high yield is dioxinone 16. Thus, a trideuteriomethyl group directs bromination away from the 2-methyl site to H-6. Bromination at the 6-position followed by loss of HBr, addition of Br2, and loss of a second HBr gives 16. Dioxinone 14, a valuable substrate for asymmetric induction studies, is formed in high yield by reductive debromination of 16. When (R)-3-hydroxybutyric acid is used in the preparation of 13, optically pure (-)-14 is obtained using the sequence described.
• Studies on the opening of dioxanone and acetal templates and application to the synthesis of 1.alpha.,25-dihydroxyvitamin D2
  作者：Juan R. Granja、Luis Castedo、Antonio Mourino

  DOI：10.1021/jo00053a024

  日期：1993.1

  The Lewis-acid-mediated nucleophilic substitution of dioxanone and acetal templates for the construction of 25-hydroxylated side chains of vitamin D2 metabolites and analogs has been studied. As an application a highly stereoselective synthesis of 1alpha,25-dihydroxyvitamin D2 by the dienyne route is described.
• SCHREIBER S. L.; REAGAN J., TETRAHEDRON LETT., 27,(1986) N 26, 2945-2948
  作者：SCHREIBER S. L.、 REAGAN J.

  DOI：——

  日期：——