3-Oxazolidinecarboxylic acid, 4-[(1S,2R)-2-hydroxy-1-(phenylmethoxy)-3-hexadecynyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4S)-

Base Information

• Chemical Name: 3-Oxazolidinecarboxylic acid, 4-[(1S,2R)-2-hydroxy-1-(phenylmethoxy)-3-hexadecynyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4S)-
• CAS No.: 194861-77-3
• Molecular Formula: C₃₃H₅₃NO₅
• Molecular Weight: 543.788
• Mol file: 194861-77-3.mol

Synonyms:

Chemical Property of 3-Oxazolidinecarboxylic acid, 4-[(1S,2R)-2-hydroxy-1-(phenylmethoxy)-3-hexadecynyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Oxazolidinecarboxylic acid, 4-[(1S,2R)-2-hydroxy-1-(phenylmethoxy)-3-hexadecynyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4S)-

There total 5 articles about 3-Oxazolidinecarboxylic acid, 4-[(1S,2R)-2-hydroxy-1-(phenylmethoxy)-3-hexadecynyl]-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: 40.0%

1-tetradecyne (765-10-6) + (4S,1'S)-4-(1'-benzyloxy-2'-oxoethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (115822-55-4) → (S)-4-((1S,2R)-1-Benzyloxy-2-hydroxy-hexadec-3-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (194861-77-3)

Guidance literature:

With triisopropoxytitanium(IV) chloride; n-butyllithium; In tetrahydrofuran; hexane; -78 deg C, 30 min; 0 deg C, 2 h; -110 deg C to RT, 12 h;

DOI:10.1016/S0040-4039(97)01340-3

Reference yield:

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) → (S)-4-((1S,2R)-1-Benzyloxy-2-hydroxy-hexadec-3-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (194861-77-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / 1.69M n-BuLi, BF₃*Et₂O, CuI / hexane; tetrahydrofuran / -50 deg C, 30 min, RT, 12 h

2: 92 percent / KHMDS / tetrahydrofuran

3: 67 percent / NBS

4: 40 percent / 1.69M n-BuLi, chlorotitanium triisopropoxide / hexane; tetrahydrofuran / -78 deg C, 30 min; 0 deg C, 2 h; -110 deg C to RT, 12 h

With triisopropoxytitanium(IV) chloride; N-Bromosuccinimide; copper(l) iodide; n-butyllithium; boron trifluoride diethyl etherate; potassium hexamethylsilazane; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4039(97)01340-3

Reference yield:

(S)-4-((S)-Benzyloxy-[1,3]dithian-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester → (S)-4-((1S,2R)-1-Benzyloxy-2-hydroxy-hexadec-3-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (194861-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / NBS

2: 40 percent / 1.69M n-BuLi, chlorotitanium triisopropoxide / hexane; tetrahydrofuran / -78 deg C, 30 min; 0 deg C, 2 h; -110 deg C to RT, 12 h

With triisopropoxytitanium(IV) chloride; N-Bromosuccinimide; n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4039(97)01340-3

upstream raw materials:

1-tetradecyne

(4S,1'S)-4-(1'-benzyloxy-2'-oxoethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(S)-4-((S)-[1,3]Dithian-2-yl-hydroxy-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester