(5R)-6-Cyano-5-hydroxy-3-oxo-hexanoic Acid tert-Butyl Ester

Base Information

• Chemical Name: (5R)-6-Cyano-5-hydroxy-3-oxo-hexanoic Acid tert-Butyl Ester
• CAS No.: 125988-01-4
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.26
• Mol file: 125988-01-4.mol

Synonyms:Hexanoic acid, 6-cyano-5-hydroxy-3-oxo-, 1,1-dimethylethyl ester, (R)-;(R)-tert-Butyl 6-cyano-5-hydroxy-3-oxohexanoate;R-tert-Butyl 6-cyano-5-hydroxy-3-oxohexanoate;

Chemical Property of (5R)-6-Cyano-5-hydroxy-3-oxo-hexanoic Acid tert-Butyl Ester

Chemical Property:

• Boiling Point: 393.204 °C at 760 mmHg
• PKA: 10.31±0.46(Predicted)
• Flash Point: 191.603 °C
• PSA: 87.39000
• Density: 1.125 g/cm³
• LogP: 0.95198
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate, Methanol

Purity/Quality:

99%, ^*data from raw suppliers

(5R)-6-Cyano-5-hydroxy-3-oxo-hexanoicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Atorvastatin 10-Trans (Atorvastatin Impurity AT10)

Technology Process of (5R)-6-Cyano-5-hydroxy-3-oxo-hexanoic Acid tert-Butyl Ester

There total 13 articles about (5R)-6-Cyano-5-hydroxy-3-oxo-hexanoic Acid tert-Butyl Ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

acetic acid tert-butyl ester (540-88-5) + (R)-ethyl 4-cyano-3-hydroxybutyrate (141942-85-0) → tert-butyl (5R)-6-cyano-5-hydroxy-3-carbonylhexanoate (125988-01-4)

Guidance literature:

acetic acid tert-butyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

(R)-ethyl 4-cyano-3-hydroxybutyrate; In tetrahydrofuran; at -40 ℃; for 4h;

Reference yield: 10.0%

sodium cyanide (143-33-9,25596-52-5) + tert-butyl (R)-6-chloro-5-hydroxy-3-oxohexanoate (404958-08-3) → tert-butyl (5R)-6-cyano-5-hydroxy-3-carbonylhexanoate (125988-01-4)

Guidance literature:

With halohydrin dehalogenase; In water; at 20 ℃; for 12h; pH=7.2; Product distribution / selectivity; Aqueous phosphate buffer;

Reference yield:

acetic acid tert-butyl ester (540-88-5) + (R)-ethyl 4-cyano-3-hydroxybutyrate (141942-85-0) → tert-butyl acetoacetate (1694-31-1) + tert-butyl (5R)-6-cyano-5-hydroxy-3-carbonylhexanoate (125988-01-4)

Guidance literature:

acetic acid tert-butyl ester; With ammonia; lithium; isoprene; In tert-butyl methyl ether; at -58 - -48 ℃; for 5h;

(R)-ethyl 4-cyano-3-hydroxybutyrate; at -45 - 20 ℃;

upstream raw materials:

t-butyl lithioacetate

(R)-ethyl 4-cyano-3-hydroxybutyrate

(R)-methyl (3-hydroxy-4-cyano)-butanoate

n-butyl (R)-(-)-4-cyano-3-hydroxybutyrate

Downstream raw materials:

1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate

(3S,5R)-tert-butyl 6-cyano-3,5-dihydroxyhexanoate

(3R,5R)-tert-butyl-6-cyano-3,5-dihydroxyhexanoate

2-((4R, 6R)-6-cyanomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid tert-butyl ester

Refernces

• 1、 -. "Preparation method of (R)-6-cyan-5-hydroxy-3-tert-butyl carbonyl hexanoate". Paragraph 0022-0023; 0025; 0027. . Retrieved 2018/06/15.
• 2、 -. "PROCESS FOR CROSSED CLAISEN CONDENSATION REACTIONS PROMOTED BY LITHIUM AMIDE IN LIQUID AMMONIA". Page/Page column 9; 10. . Retrieved 2014/02/15.