CarbaMic acid, N-[(1S,3R)-1,3-bis(hydroxyMethyl)-5-hexen-1-yl]-, 1,1-diMethylethyl ester

Base Information

• Chemical Name: CarbaMic acid, N-[(1S,3R)-1,3-bis(hydroxyMethyl)-5-hexen-1-yl]-, 1,1-diMethylethyl ester
• CAS No.: 942144-12-9
• Molecular Formula: C₁₃H₂₅NO₄
• Molecular Weight: 259.346
• Mol file: 942144-12-9.mol

Synonyms:CarbaMic acid, N-[(1S,3R)-1,3-bis(hydroxyMethyl)-5-hexen-1-yl]-, 1,1-diMethylethyl ester

Chemical Property of CarbaMic acid, N-[(1S,3R)-1,3-bis(hydroxyMethyl)-5-hexen-1-yl]-, 1,1-diMethylethyl ester

Chemical Property:

• PSA: 82.28000
• LogP: 1.65110
• Storage Temp.: 2-8°C

Purity/Quality:

98%Min ^*data from raw suppliers

tert-Butyl((2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-yl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CarbaMic acid, N-[(1S,3R)-1,3-bis(hydroxyMethyl)-5-hexen-1-yl]-, 1,1-diMethylethyl ester

There total 2 articles about CarbaMic acid, N-[(1S,3R)-1,3-bis(hydroxyMethyl)-5-hexen-1-yl]-, 1,1-diMethylethyl ester 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: 85.0%

(2S,4R)-1-tert-butyl 4-allyl-2-ethoxycarbonyl-5-oxopyrrolidine-1-carboxylate (153080-81-0) → tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate (942144-12-9)

Guidance literature:

(2S,4R)-1-tert-butyl 4-allyl-2-ethoxycarbonyl-5-oxopyrrolidine-1-carboxylate; With sodium tetrahydroborate; In methanol; water; at 20 ℃; for 1h;

With water; ammonium chloride; In methanol;

Reference yield:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate (942144-12-9)

Guidance literature:

Multi-step reaction with 2 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

With sodium tetrahydroborate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; water;

DOI:10.1021/ml200137x

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;

upstream raw materials:

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

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

Downstream raw materials:

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