Tert-butyl (R)-6-chloro-5-hydroxy-3-oxohexanoate

Base Information

• Chemical Name: Tert-butyl (R)-6-chloro-5-hydroxy-3-oxohexanoate
• CAS No.: 404958-08-3
• Molecular Formula: C10H17ClO4
• Molecular Weight: 236.696
• DSSTox Substance ID: DTXSID50426933
• Nikkaji Number: J1.664.033F
• Wikidata: Q82239716
• Mol file: 404958-08-3.mol

Synonyms:404958-08-3;TERT-BUTYL (R)-6-CHLORO-5-HYDROXY-3-OXOHEXANOATE;tert-butyl (5R)-6-chloro-5-hydroxy-3-oxohexanoate;tert-Butyl 6-Chloro-(R)-hydroxy-3-oxohexanoate;404958-69-6;starbld0001086;DTXSID50426933;Hexanoic acid, 6-chloro-5-hydroxy-3-oxo-, 1,1-dimethylethyl ester, (5R)-;CS-0165339;(R)-3-Oxo-5-hydroxy-6-chlorohexanoic acid tert-butyl ester;(5R)-6-Chloro-5-hydroxy-3-oxo-hexanoic Acid 1,1-Dimethylethyl Ester;(R)-tert-butyl 6-chloro-5-hydroxy-3-oxohexanoate? (Rosuvastatin Impurity pound(c)

Chemical Property of Tert-butyl (R)-6-chloro-5-hydroxy-3-oxohexanoate

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 236.0815367
• Heavy Atom Count: 15
• Complexity: 232

Purity/Quality:

>95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(=O)CC(CCl)O
• Isomeric SMILES: CC(C)(C)OC(=O)CC(=O)C[C@H](CCl)O

Technology Process of Tert-butyl (R)-6-chloro-5-hydroxy-3-oxohexanoate

There total 1 articles about Tert-butyl (R)-6-chloro-5-hydroxy-3-oxohexanoate 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:

tert-butyl 6-chloro-3,5-dioxohexanoate (276249-18-4) → Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate (154026-92-3) + tert-butyl (R)-6-chloro-5-hydroxy-3-oxohexanoate (404958-08-3)

Guidance literature:

With Amberlite^TM XAD-7 resin; baker's yeast whole cells; In water; at 20 ℃; for 15h; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2004.07.045

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:

tert-butyl (R)-6-chloro-5-hydroxy-3-oxohexanoate (404958-08-3) → (2'R,6'R,1E,3Z,5R)-(+)-7-tert-butyldiphenylsilyloxy-1-(5',6'-dihydro-2'H-2'-isopropoxypyran-6'-yl)-3-ethyl-5-methylhepta-1,3-diene (410523-53-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaBH₄ / ethanol / 0 °C

1.2: 78 percent / p0TsOH / toluene / Heating

2.1: DIBAl-H / CH₂Cl₂ / -78 °C

3.1: PPTS / benzene / 60 °C

4.1: 1-methyl-pyrrolidin-2-one / 85 °C

5.1: K₂CO₃ / methanol / 20 °C

6.1: 82 mg / KO^tBu / toluene; tetrahydrofuran / 1 h / 0 °C

With sodium tetrahydroborate; potassium tert-butylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; toluene; benzene; 6.1: Swern oxidation / 7.1: Wittig reaction;

DOI:10.1021/ol0256116

upstream raw materials:

tert-butyl 6-chloro-3,5-dioxohexanoate

Downstream raw materials:

(2'R,6'R,1E,3Z,5R)-(+)-7-tert-butyldiphenylsilyloxy-1-(5',6'-dihydro-2'H-2'-isopropoxypyran-6'-yl)-3-ethyl-5-methylhepta-1,3-diene

(S)-6-chloromethyl-5,6-dihydropyran-2-one

tert-butyl (5R)-6-cyano-5-hydroxy-3-carbonylhexanoate

Refernces

• 1、 Wolberg, Michael,Kaluzna, Iwona A.,Mueller, Michael,Stewart, Jon D.. "Regio and enantioselective reduction of t-butyl 6-chloro-3,5-dioxohexanoate with baker's yeast". . p. 2825 - 2828. Retrieved 2007/10/03.