1,1-Dimethylethyl (S)-5-hydroxy-3-oxo-6-(triphenylmethoxy)hexanoate | 113240-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,1-Dimethylethyl (S)-5-hydroxy-3-oxo-6-(triphenylmethoxy)hexanoate
• 英文别名: tert-butyl 6-triphenylmethyloxy-5(S)-hydroxy-3-oxohexanoate；(5S)-5-hydroxy-3-oxo-6-trityloxyhexanoic acid tert-butyl ester；tert.-Butyl 5S-hydroxy-6-triphenylmethoxy-3-oxohexanoate；t-Butyl (S)-5-hydroxy-3-oxo-6-(triphenylmethoxy)hexanoate；tert-butyl (5S)-5-hydroxy-3-oxo-6-trityloxyhexanoate
• CAS: 113240-61-2
• 化学式: C₂₉H₃₂O₅
• 分子量: 460.57
• InChiKey: GAJZMSCUUOBKDJ-SANMLTNESA-N

物化性质

• 沸点：
  587.3±50.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1-Dimethylethyl (S)-5-hydroxy-3-oxo-6-(triphenylmethoxy)hexanoate 在 咪唑 、 sodium tetrahydroborate 、 二乙基甲氧基硼烷 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1,1-Dimethylethyl (3R,5S)-3,5-di-[(1',1'-dimethylethyl)-diphenylsilyloxy]-6-(triphenylmethoxy)hexanoate
  参考文献：
  名称：

  A highly stereoselective route to the four stereoisomers of a six-carbon synthon

  摘要：

  DOI：

  10.1016/s0957-4166(00)86320-x
• 作为产物：
  描述：

  (S)-methyl 3-hydroxy-4-(trityloxy)butanoate 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 1,1-Dimethylethyl (S)-5-hydroxy-3-oxo-6-(triphenylmethoxy)hexanoate
  参考文献：
  名称：

  Novel boronate esters

  摘要：

  本发明涉及光学活性硼酸酯衍生物，可用作合成HMG-CoA酶抑制剂（如阿托伐他汀、西立伐他汀、洛伐他汀、匹伐他汀和氟伐他汀）的中间体。

  公开号：

  US20060040898A1

文献信息

• Process for the production of 3,5,6-trihydroxyhexanoic acid derivative
  申请人：Kanegafuchi Chemical Industry Co., Ltd.

  公开号：US04983759A1

  公开（公告）日：1991-01-08

  A compound of a 3,5,6-trihydroxyhexanoic acid derivative of the formula: ##STR1## wherein P.sup.1 and P.sup.2 are independently hydrogen atoms or hydroxy-protecting groups, or together form a ring, and R is an alkyl group is effectively prepared by a process comprising steps of: reacting a butyronitrile derivative of the formula: ##STR2## wherein P.sup.1 and P.sup.2 are the same as defined above with an .alpha.-haloacetate of the formula: X--CH.sub.2 --COOR (III) wherein X is a halogen atom, and R is the same as defined above in the presence of a metallic catalyst selected from the group consisting zinc and zinc-copper to form a keto acid derivative of the formula: ##STR3## wherein P.sup.1, P.sup.2 and R are the same as defined above, and then reducing the obtained keto-acid derivative of the formula (IV).

  一种化合物，其为3,5,6-三羟基己酸衍生物，化学式如下：##STR1## 其中P1和P2分别是氢原子或羟基保护基，或者一起形成一个环，R为烷基基团，通过以下步骤有效制备：将以下化学式的丁腈衍生物：##STR2## 其中P1和P2的定义与上述相同，与以下化学式的α-卤代乙酸酯：X--CH2--COOR (III) 反应，其中X为卤素原子，R的定义与上述相同，在选择自锌和锌-铜组成的金属催化剂存在下，形成以下酮酸衍生物：##STR3## 其中P1、P2和R的定义与上述相同，然后还原得到的酮酸衍生物（IV）。
• Pyrimidinyl-substituted hydroxyacids, lactones and esters and pharmaceutical compositions containing them
  申请人：SANDOZ AG

  公开号：EP0367895A1

  公开（公告）日：1990-05-16

  Compounds of formula I wherein R¹, R², Q, X and Y have various significances, in free acid form, or in the form of an ester or δ-lactone thereof, or in salt form as appropriate, are described. They are indicated for use as hypolipoproteinemic and anti-atherosclerotic agents. They may be obtained by reduction, hydrolysis, deprotection or oxidation of appropriate starting compounds, and variously interconverted by e.g. hydrolysis, salt formation, esterification and/or lactonisation.

  式I中的化合物，其中R¹、R²、Q、X和Y具有不同的含义，在游离酸形式中，或者以其酯或δ-内酯的形式，或者以盐的形式描述。它们被指定用作降低脂蛋白和抗动脉粥样硬化药物。它们可以通过还原、水解、去保护或氧化适当的起始化合物获得，并通过水解、盐形成、酯化和/或内酯化等方法进行各种互变。
• Processes for the synthesis of diprotected
  申请人：Sandoz Pharm. Corp.

  公开号：US04870199A1

  公开（公告）日：1989-09-26

  Process for the synthesis of compounds of the formula ##STR1## in R[R*,S*] enantiomeric form, wherein each P.sub.1 is independently an hydroxy group-protecting group, and R.sub.2z is C.sub.1-4 alkyl, benzyl or allyl, comprising, as a key step when R.sub.2z is R.sub.2x, the reaction of the compound of the formula ##STR2## in (S) enantiomeric form with a compound of the formula Mg.sup. .circle.+2 (.sup..crclbar. OOC--CH.sub.2 --COOR.sub.2x).sub.2 to obtain a compound of the formula ##STR3## in (S) enantiomeric form, and, as a key step when R.sub.2z is R.sub.2y, the reaction of a compound of the formula ##STR4## in (S) enantioimeric form with a compound of the formula Li.sup..sym..crclbar. CH.sub.2 --COOR.sub.2y to obtain a compound of the formula ##STR5## in (S) enantiomeric form, wherein R.sub.2x is primary or secondary C.sub.1-4 alkyl, benzyl or allyl, R.sub.2y is C.sub.1-4 alkyl not containing an asymmetric carbon atom, and R.sub.3 ' is methyl or ethyl, processes for the synthesis of compounds of the formula ##STR6## comprising reacting a compound of the formula ##STR7## with the reaction product of a strong base and a compound of the formula ##STR8## optionally followed by, when R.sub.2z is allyl, cleavage of the allyl and P.sub.1 groups to obtain the corresponding compound of the formula ##STR9## wherein each R.sub.7 is methyl or ethyl, R is as defined in the specification, and each P.sub.1 independently and R.sub.2z are as defined above, and the compounds of the formula ##STR10## wherein R and each R.sub.7 are as defined above.

  合成具有以下结构的化合物的过程##STR1##以R[R*,S*]对映体形式存在，其中每个P.sub.1独立地是一个羟基保护基团，而R.sub.2z是C.sub.1-4烷基，苄基或烯丙基，包括作为关键步骤的情况，当R.sub.2z是R.sub.2x时，将具有以下结构的化合物##STR2##以(S)对映体形式与具有以下结构的化合物发生反应 Mg.sup. .circle.+2 (.sup..crclbar. OOC--CH.sub.2 --COOR.sub.2x).sub.2 以获得具有以下结构的化合物##STR3##以(S)对映体形式，并且作为关键步骤的情况，当R.sub.2z是R.sub.2y时，将具有以下结构的化合物##STR4##以(S)对映异构体形式与具有以下结构的化合物反应 Li.sup..sym..crclbar. CH.sub.2 --COOR.sub.2y 以获得具有以下结构的化合物##STR5##以(S)对映体形式，其中R.sub.2x是初级或次级C.sub.1-4烷基，苄基或烯丙基，R.sub.2y是不含手性碳原子的C.sub.1-4烷基，而R.sub.3 '是甲基或乙基，合成具有以下结构的化合物的过程##STR6##包括将具有以下结构的化合物##STR7##与强碱和具有以下结构的化合物的反应产物进行反应##STR8##，随后可选地，当R.sub.2z是烯丙基时，裂解烯丙基和P.sub.1基团以获得相应的具有以下结构的化合物##STR9##其中每个R.sub.7是甲基或乙基，R如规范中定义的那样，每个P.sub.1独立地和R.sub.2z如上所述定义，并且具有以下结构的化合物##STR10##其中R和每个R.sub.7如上所定义。
• [EN] NOVEL PROCESS FOR STEREOSELECTIVE REDUCTION OF ß-KETOESTERS<br/>[FR] NOUVEAU PROCEDE POUR UNE REDUCTION STEREOSELECTIVE DE DOLLAR G(B)-SETOESTERS
  申请人：BIOCON LTD

  公开号：WO2004094343A1

  公开（公告）日：2004-11-04

  A novel process for the preparation of compounds of formula (I): R1 = CN, OP (P=any suitable protecting group), alkyl, aryl or hetroaryl, R2 = Alkyl or aryl by reacting a compound of formula (II): R1 = CN, OP (P=any suitable protecting group), alkyl, aryl or hetroaryl, R2 = Alkyl or aryl with a reducing agent, sodium borohydride in presence of metal halides, preferably CeC13 or metal alkoxides, preferably Ti(OiPr)4.

  一种制备式（I）化合物的新工艺：其中R1 = CN，OP（P = 任何适当的保护基），烷基，芳基或杂芳基，R2 = 烷基或芳基，通过将式（II）化合物与还原剂钠硼氢化物在金属卤化物（优选为CeCl3）或金属烷氧化物（优选为Ti（OiPr）4）存在下反应。
• Boronate esters
  申请人：Biocon Limited

  公开号：US07238826B2

  公开（公告）日：2007-07-03

  The present invention relates to optically active boronate derivatives which are useful as intermediates for the synthesis of HMG-CoA enzyme inhibitors such as atorvastatin, cerivastatin, rosuvastatin, pitavastatin, and fluvastatin.

  本发明涉及光学活性硼酸酯衍生物，可用作合成HMG-CoA酶抑制剂（如阿托伐他汀，西立伐他汀，罗伐他汀，匹伐他汀和氟伐他汀）的中间体。