(S)-tert-butyl 3-hydroxybutanoate

Base Information

• Chemical Name: (S)-tert-butyl 3-hydroxybutanoate
• CAS No.: 82578-45-8
• Molecular Formula: C8H16O3
• Molecular Weight: 160.213
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID50436219
• Nikkaji Number: J343.959C
• Wikidata: Q72503290
• Mol file: 82578-45-8.mol

Synonyms:82578-45-8;(S)-tert-butyl 3-hydroxybutanoate;(S)-3-Hydroxy-butyric acid tert-butyl ester;tert-butyl (3S)-3-hydroxybutanoate;(S)-3-Hydroxybutyric acid tert-butyl ester;Butanoic acid, 3-hydroxy-, 1,1-dimethylethyl ester, (3S)-;(+)-tert-Butyl(S)-3-hydroxybutyrate;(S)-tert-Butyl3-hydroxybutanoate;SCHEMBL607503;(s)-t-butyl-3-hydroxybutanoate;DTXSID50436219;PKPVFILAHLKSNJ-LURJTMIESA-N;tert-butyl (S)-3-hydroxybutyrate;Tert-butyl (S)-3-hydroxybutanoate;MFCD00040559;AKOS015913254;DS-1196;tert-Butyl (S)-(+)-3-hydroxybutyrate;(3S)-3-Hydroxybutyric acid tert-butyl ester;CS-0313136;A848097;3-Hydroxy-butyric acid tert-butyl ester;(S)-tert-Butyl 3-hydroxybutanoate

Chemical Property of (S)-tert-butyl 3-hydroxybutanoate

Chemical Property:

• Refractive Index: n20/D 1.422
• Boiling Point: 228.251 °C at 760 mmHg
• PKA: 14.40±0.20(Predicted)
• Flash Point: 87.3 °C
• PSA: 46.53000
• Density: 0.989 g/cm³
• LogP: 1.09900
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 160.109944368
• Heavy Atom Count: 11
• Complexity: 135

Purity/Quality:

98%min ^*data from raw suppliers

(S)-3-Hydroxy-butyricacidtert-butylester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-tert-butyl 3-hydroxybutanoate

There total 10 articles about (S)-tert-butyl 3-hydroxybutanoate 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: 100.0%

tert-butyl acetoacetate (1694-31-1) → tert-butyl (S)-3-hydroxybutyrate (82578-45-8) + tert-butyl (R)-3-hydroxybutanoate (110171-06-7)

Guidance literature:

With hydrogen; C₅₀H₄₄Cl₂N₂O₈P₄Ru^(4-)*Zr⁽⁴⁺⁾; In methanol; at 20 ℃; for 20h; under 72402.6 Torr; Product distribution / selectivity;

Reference yield: 96.5%

tert-butyl acetoacetate (1694-31-1) → tert-butyl (S)-3-hydroxybutyrate (82578-45-8)

Guidance literature:

With hydrogen; In tert-butyl alcohol; at 80 ℃; for 10h; under 15001.5 Torr; enantioselective reaction;

DOI:10.1039/c5ra23597a

Reference yield: 94.0%

Isopropenyl acetate (108-22-5) + tert-butyl 3-hydroxybutyrate (90435-23-7) → tert-butyl (S)-3-hydroxybutyrate (82578-45-8) + tert-butyl (R)-3-hydroxybutanoate (110171-06-7) + (R)-3-acetoxy-butyric acid tert-butyl ester (120444-06-6)

Guidance literature:

With Pseudomonas cepacia lipase immobilized on ceramic; potassium tert-butylate; sodium carbonate; [2,3,4,5-Ph4(η⁵-C4CNH(i-Pr))]Ru(CO)2Cl; In toluene; at 25 ℃; for 120h;

DOI:10.1021/jo0355799

upstream raw materials:

tert-butyl acetoacetate

(R)-3-Hydroxy-4-((R)-toluene-4-sulfinyl)-butyric acid tert-butyl ester

(S)-3-Acetoxy-butyric acid tert-butyl ester

Isopropenyl acetate

Downstream raw materials:

(2S,3S)-tert-butyl-2-benzyl-3-hydroxybutanoate

(2S,3S,4S)-4-Methoxycarbonylamino-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-carboxylic acid tert-butyl ester

(R,R,R,R,R,R,R,S)-α-benzyl-ω-(tert-butoxy)octakis

(R,R,R,R,R,R,S,S)-α-benzyl-ω-(tert-butoxy)octakis

Refernces

• 1、 Tanaka, Shusei,Kojima, Hideo,Takeda, Satomi,Yamanaka, Rio,Takemura, Tetsuo. "Asymmetric visible-light photobiocatalytic reduction of β-keto esters utilizing the cofactor recycling system in Synechocystis sp. PCC 6803". supporting information. . Retrieved 2020/05/08.
• 2、 Wang, Tao,Lyu, Yuan,Chen, Xingkun,Li, Cunyao,Jiang, Miao,Song, Xiangen,Ding, Yunjie. "Ru coordinated with BINAP in knitting aryl network polymers for heterogeneous asymmetric hydrogenation of methyl acetoacetate". . p. 28447 - 28450. Retrieved 2016/04/08.