tert-butyl (2R,3R)-1,3-dihydroxy-5-phenylpent-4-yn-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (2R,3R)-1,3-dihydroxy-5-phenylpent-4-yn-2-ylcarbamate
• CAS No.: 906528-91-4
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• Mol file: 906528-91-4.mol

Synonyms:tert-butyl (2R,3R)-1,3-dihydroxy-5-phenylpent-4-yn-2-ylcarbamate

Chemical Property of tert-butyl (2R,3R)-1,3-dihydroxy-5-phenylpent-4-yn-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,3R)-1,3-dihydroxy-5-phenylpent-4-yn-2-ylcarbamate

There total 3 articles about tert-butyl (2R,3R)-1,3-dihydroxy-5-phenylpent-4-yn-2-ylcarbamate 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%

(R)-tert-butyl 4-((R)-1'-hydroxy-3-phenylprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate (906528-89-0) → tert-butyl (2R,3R)-1,3-dihydroxy-5-phenylpent-4-yn-2-ylcarbamate (906528-91-4)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 36h;

DOI:10.1016/j.bmc.2006.03.048

Reference yield:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → tert-butyl (2R,3R)-1,3-dihydroxy-5-phenylpent-4-yn-2-ylcarbamate (906528-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / ZnBr₂ / tetrahydrofuran; diethyl ether / -78 - 20 °C

2: 70 percent / p-TsOH*H₂O / methanol / 36 h / 20 °C

With toluene-4-sulfonic acid; zinc dibromide; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/j.bmc.2006.03.048

Reference yield:

lithium phenylacetylide (4440-01-1) → tert-butyl (2R,3R)-1,3-dihydroxy-5-phenylpent-4-yn-2-ylcarbamate (906528-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / ZnBr₂ / tetrahydrofuran; diethyl ether / -78 - 20 °C

2: 70 percent / p-TsOH*H₂O / methanol / 36 h / 20 °C

With toluene-4-sulfonic acid; zinc dibromide; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/j.bmc.2006.03.048

upstream raw materials:

(R)-tert-butyl 4-((R)-1'-hydroxy-3-phenylprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

lithium phenylacetylide

Downstream raw materials:

N-((2R,3R)-3-hydroxy-1-morpholino-5-phenylpent-4-yn-2-yl)palmitamide

N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide

(4R,5R)-tert-butyl 4-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-5-(2-phenylethynyl)oxazolidine-3-carboxylate