3-Oxazolidinecarboxylic acid, 4-[(2R)-2-(hydroxyMethyl)-4-penten-1-yl]-2,2-diMethyl-, 1,1-diMethylethyl ester, (4S)-

Base Information

• Chemical Name: 3-Oxazolidinecarboxylic acid, 4-[(2R)-2-(hydroxyMethyl)-4-penten-1-yl]-2,2-diMethyl-, 1,1-diMethylethyl ester, (4S)-
• CAS No.: 942144-13-0
• Molecular Formula: C₁₆H₂₉NO₄
• Molecular Weight: 299.411
• Hs Code.: 2934999090
• Mol file: 942144-13-0.mol

Synonyms:3-Oxazolidinecarboxylic acid, 4-[(2R)-2-(hydroxyMethyl)-4-penten-1-yl]-2,2-diMethyl-, 1,1-diMethylethyl ester, (4S)-

Chemical Property of 3-Oxazolidinecarboxylic acid, 4-[(2R)-2-(hydroxyMethyl)-4-penten-1-yl]-2,2-diMethyl-, 1,1-diMethylethyl ester, (4S)-

Chemical Property:

• PSA: 59.00000
• LogP: 2.87100
• Storage Temp.: 2-8°C

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-tert-Butyl4-((R)-2-(hydroxymethyl)pent-4-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Oxazolidinecarboxylic acid, 4-[(2R)-2-(hydroxyMethyl)-4-penten-1-yl]-2,2-diMethyl-, 1,1-diMethylethyl ester, (4S)-

There total 3 articles about 3-Oxazolidinecarboxylic acid, 4-[(2R)-2-(hydroxyMethyl)-4-penten-1-yl]-2,2-diMethyl-, 1,1-diMethylethyl ester, (4S)- 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: 96.0%

tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate (942144-12-9) + 2,2-dimethoxy-propane (77-76-9) → (S)-tert-butyl 4-((R)-2-(hydroxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (942144-13-0)

Guidance literature:

tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate; 2,2-dimethoxy-propane; With toluene-4-sulfonic acid; In acetone; at -20 - 20 ℃; for 1h;

With triethylamine; In acetone; at 20 ℃; for 0.0833333h;

Reference yield:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → (S)-tert-butyl 4-((R)-2-(hydroxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (942144-13-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 2 h / -78 °C

2.1: sodium tetrahydroborate / methanol; water / 1 h / 20 °C

3.1: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C

With sodium tetrahydroborate; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; water; acetone;

DOI:10.1021/ml200137x

Reference yield:

(2S,4R)-1-tert-butyl 4-allyl-2-ethoxycarbonyl-5-oxopyrrolidine-1-carboxylate (153080-81-0) → (S)-tert-butyl 4-((R)-2-(hydroxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (942144-13-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol; water / 1 h / 20 °C

2: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C

With sodium tetrahydroborate; toluene-4-sulfonic acid; In methanol; water; acetone;

DOI:10.1021/ml200137x

upstream raw materials:

tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate

2,2-dimethoxy-propane

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

(2S,4R)-1-tert-butyl 4-allyl-2-ethoxycarbonyl-5-oxopyrrolidine-1-carboxylate

Downstream raw materials:

(S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-1-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

(S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxypentyl)-2,2-dimethyloxazolidine-3-carboxylate