(3R,5S)-tert-Butyl 6-chloro-3,5-dihydroxyhexanoate

Base Information

• Chemical Name: (3R,5S)-tert-Butyl 6-chloro-3,5-dihydroxyhexanoate
• CAS No.: 154026-93-4
• Molecular Formula: C10H19ClO4
• Molecular Weight: 238.711
• DSSTox Substance ID: DTXSID10431205
• Nikkaji Number: J1.476.618I
• Wikidata: Q82245029
• Mol file: 154026-93-4.mol

Synonyms:154026-93-4;(3R,5S)-tert-Butyl 6-chloro-3,5-dihydroxyhexanoate;Tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate;Hexanoic acid, 6-chloro-3,5-dihydroxy-, 1,1-dimethylethyl ester, (3R,5S)-;(3R,5S)-6-Chloro-3,5-dihydroxyhexanoic Acid tert-Butyl Ester;(3R,5S)-tert-Butyl6-chloro-3,5-dihydroxyhexanoate;SCHEMBL1260626;DTXSID10431205;FIKPWJZUGTVXCO-SFYZADRCSA-N;AKOS015918488;AM85025;CS-0165341;A809490;t-butyl (3r,5s)-6-chloro-3,5-dihydroxyhexanoate;Tert-butyl(3R,5S)-6-chloro-3,5-dihydroxyhexanoate;(3R,5S)-3,5-Dihydroxy-6-chlorohexanoic acid tert-butyl ester;(3R,5S)-tert-butyl 6-chloro-3,5-dihydroxyhexanoate? (Rosuvastatin Impurity pound(c)

Chemical Property of (3R,5S)-tert-Butyl 6-chloro-3,5-dihydroxyhexanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.479
• Boiling Point: 364.584 °C at 760 mmHg
• PKA: 13.69±0.20(Predicted)
• Flash Point: 174.295 °C
• PSA: 66.76000
• Density: 1.169 g/cm³
• LogP: 1.06890
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 238.0971868
• Heavy Atom Count: 15
• Complexity: 200

Purity/Quality:

99%, ^*data from raw suppliers

(3R,5S)-6-Chloro-3,5-dihydroxyhexanoicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(CC(CCl)O)O
• Isomeric SMILES: CC(C)(C)OC(=O)C[C@@H](C[C@@H](CCl)O)O
• Uses: (3R,5S)-6-Chloro-3,5-dihydroxyhexanoic Acid tert-Butyl Ester is an intermediate in the synthesis of Rosuvastatin (R700500), a selective, competitive HMG-CoA reductase inhibitor.

Technology Process of (3R,5S)-tert-Butyl 6-chloro-3,5-dihydroxyhexanoate

There total 9 articles about (3R,5S)-tert-Butyl 6-chloro-3,5-dihydroxyhexanoate 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%

Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate (154026-92-3) → 1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate (154026-93-4)

Guidance literature:

With carbonyl reductase Phe₁₄₅Tyr/Thr₁₅₂Ser mutant; NADPH; In aq. phosphate buffer; isopropyl alcohol; at 30 ℃; for 8h; pH=7; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1016/j.bioorg.2018.07.025

Reference yield: 95.5%

tert-butyl 6-chloro-3,5-dioxohexanoate (276249-18-4) → 1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate (154026-93-4)

Guidance literature:

With hydrogen; (R)-[RuCl₂(BINAP)]n; In ethanol; at 95 - 105 ℃; for 0.666667 - 480h; under 67506.8 - 75007.5 Torr; Conversion of starting material;

Reference yield:

Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate (154026-92-3) → 1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate (154026-93-4) + tert-butyl anti-(3S,5S)-6-chloro-3,5-dihydroxyhexanoate

Guidance literature:

Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate; With diethyl methoxy borane; In tetrahydrofuran; methanol; at -70 ℃; for 0.333333h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -70 ℃; for 3h;

DOI:10.1002/1521-3773(20001201)39:23<4306::AID-ANIE4306>3.0.CO;2-G

upstream raw materials:

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

tert-butyl acetoacetate

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

acetic acid tert-butyl ester

Downstream raw materials:

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

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

Refernces

• 1、 Liu, Zhi-Qiang,Wu, Lin,Zhang, Xiao-Jian,Xue, Ya-Ping,Zheng, Yu-Guo. "Directed Evolution of Carbonyl Reductase from Rhodosporidium toruloides and Its Application in Stereoselective Synthesis of tert-Butyl (3R,5S)-6-Chloro-3,5-dihydroxyhexanoate". . p. 3721 - 3729. Retrieved 2017.
• 2、 Xu, Tingting,Wang, Can,Zhu, Shaozhou,Zheng, Guojun. "Enzymatic preparation of optically pure t-butyl 6-chloro-(3R,5S)-dihydroxyhexanoate by a novel alcohol dehydrogenase discovered from Klebsiella oxytoca". . p. 72 - 79. Retrieved 2017/05/24.