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

Base Information

• Chemical Name: (R)-tert-butyl 4-((R)-1'-hydroxy-3-phenylprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 906528-89-0
• Molecular Formula: C₁₉H₂₅NO₄
• Molecular Weight: 331.412

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

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

Chemical Property:

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

There total 2 articles about (R)-tert-butyl 4-((R)-1'-hydroxy-3-phenylprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate 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: 44.0%

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) + lithium phenylacetylide (4440-01-1) → (R)-tert-butyl 4-((R)-1'-hydroxy-3-phenylprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate (906528-89-0) + (R)-tert-butyl 4-((S)-1'-hydroxy-3-phenylprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:

With zinc dibromide; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃;

DOI:10.1016/j.bmc.2006.03.048

Reference yield:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) + phenylacetylene (536-74-3) → (R)-tert-butyl 4-((R)-1'-hydroxy-3-phenylprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate (906528-89-0) + (R)-tert-butyl 4-((S)-1'-hydroxy-3-phenylprop-2'-ynyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:

With johnphos; acetylacetonatodicarbonylrhodium(l); In tetrahydrofuran; at 40 ℃;

DOI:10.1021/jo701643h

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

upstream raw materials:

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

lithium phenylacetylide

phenylacetylene

Downstream raw materials:

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

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

(4R,5R)-tert-butyl 2,2-dimethyl-5-(2-phenylethynyl)-4-((pyrrolidin-1-yl)methyl)oxazolidine-3-carboxylate

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

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