(+)-tert-Butyl D-lactate

Base Information

• Chemical Name: (+)-tert-Butyl D-lactate
• CAS No.: 68166-83-6
• Molecular Formula: C7H14 O3
• Molecular Weight: 146.186
• Hs Code.: 2918110000
• European Community (EC) Number: 851-863-2
• DSSTox Substance ID: DTXSID40449515
• Nikkaji Number: J70.596I
• Wikidata: Q82269014
• Mol file: 68166-83-6.mol

Synonyms:68166-83-6;(+)-tert-Butyl D-lactate;TERT-BUTYL (R)-(+)-LACTATE;TERT-BUTYL (2R)-2-HYDROXYPROPANOATE;(R)-tert-butyl 2-hydroxypropanoate;D-Lactic acid tert-butyl ester;2-(R)-hydroxypropionic acid tert-butyl ester;MFCD00191884;tert-butyl (R)-lactate;(R)-(+)-Lactic acid tert-butyl ester;tert-butyl(R)-lactate;(+)-t-Butyl D-lactate;tert-butyl D-(-)-lactate;tert-butyl(R)-(+)-lactate;tert-butyl (r)-(+) lactate;SCHEMBL1332536;(R)-t-butyl-2-hydroxypropanoate;DTXSID40449515;IXXMVXXFAJGOQO-RXMQYKEDSA-N;(R)-tert-butyl2-hydroxypropanoate;tert-butyl(2r)-2-hydroxypropanate;CS-B0165;tert-butyl (R)-2-hydroxypropanoate;tert-butyl (2R)-2-hydroxypropanate;AKOS017343714;tert-Butyl (R)-(+)-lactate, 99%;AS-62908;(R)-2-hydroxy-propionic acid tert-butyl ester;EN300-310624;P17851;Propanoicacid,2-hydroxy-,1,1-dimethylethyl ester,(2R)-;(+)-tert-Butyl D-lactate, >=99.0% (sum of enantiomers, GC)

Chemical Property of (+)-tert-Butyl D-lactate

Chemical Property:

• Vapor Pressure: 0.77mmHg at 25°C
• Melting Point: 38-42oC
• Boiling Point: 161.821°C at 760 mmHg
• PKA: 13.07±0.20(Predicted)
• Flash Point: 113 °C
• PSA: 46.53000
• Density: 1.005g/cm³
• LogP: 0.70890
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 146.094294304
• Heavy Atom Count: 10
• Complexity: 123

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-tert-Butyl2-hydroxypropanoate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Useful:

• Canonical SMILES: CC(C(=O)OC(C)(C)C)O
• Isomeric SMILES: C[C@H](C(=O)OC(C)(C)C)O
• Uses: (R)-tert-Butyl 2-hydroxypropanoate is an intermediate used in the stereo controlled synthesis of hydroxy carboxylic acids from L-amino acids.

Technology Process of (+)-tert-Butyl D-lactate

There total 6 articles about (+)-tert-Butyl D-lactate 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: 70.0%

4-Nitro-benzoic acid (R)-1-tert-butoxycarbonyl-ethyl ester (111505-48-7) → D-lactic acid t-butyl ester (68166-83-6)

Guidance literature:

With hydrazine hydrate; NaOH, pH= 10;

DOI:10.1016/S0040-4039(00)95997-5

Reference yield: 38.0%

(+/-)-lactyl butyrate tert-butyl ester → D-lactic acid t-butyl ester (68166-83-6)

Guidance literature:

for 22h; enzymatic hydrolysis with lipase from Pseudomonas cepacia, phosphate buffer, pH= 6.9 to 7.1;

DOI:10.1021/jo00008a016

Reference yield:

t-butyl pyruvate (76849-54-2) → D-lactic acid t-butyl ester (68166-83-6) + (+)-tert-butyl D-lactate (13650-70-9)

Guidance literature:

With potassium 9-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclo<3.3.1>nonane; In tetrahydrofuran; at -78 ℃; for 8h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00241a021

upstream raw materials:

t-butyl pyruvate

t-butyl 2(R)-acetoxypropionate

4-Nitro-benzoic acid (R)-1-tert-butoxycarbonyl-ethyl ester

tert-butyl alcohol

Downstream raw materials:

tert-butyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-D-lactate

tert-butyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-glucopyranosyl)-D-lactate

L-phenylalanyl D-lactic acid t-butyl ester

D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactic acid t-butyl ester

Refernces

• 1、 Kazlauskas, Romas J.,Weissfloch, Alexandra N. E.,Rappaport, Aviva T.,Cuccia, Louis A.. "A Rule To Predict Which Enantiomer of a Secondary Alcohol Reacts Faster in Reactions Catalyzed by Cholesterol Esterase, Lipase from Pseudomonas cepacia, and Lipase from Candida rugosa". . p. 2656 - 2665. Retrieved 2007/10/02.
• 2、 Scilimati, A.,Ngooi, T. K.,Sih, Charles J.. "BIOCATALYTIC RESOLUTION OF (+/-)-HYDROXYALKANOIC ESTERS. A STRATEGY FOR ENHANCING THE ENANTIOMERIC SPECIFICITY OF LIPASE-CATALYZED ESTER HYDROLYSIS.". . p. 4927 - 4930. Retrieved 2007/10/02.