(4R,5S)-tert-butyl 4-((R)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

Chemical Name:(4R,5S)-tert-butyl 4-((R)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate
CAS No.:1437250-09-3
Molecular Formula:C₂₆H₃₉NO₆
Molecular Weight:461.599
Hs Code.:

Synonyms:(4R,5S)-tert-butyl 4-((R)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate

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Chemical Property of (4R,5S)-tert-butyl 4-((R)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property:

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Useful:

Technology Process of (4R,5S)-tert-butyl 4-((R)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate

There total 9 articles about (4R,5S)-tert-butyl 4-((R)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-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:

: 1437250-12-8
(4R,5S)-tert-butyl 5-((4-methoxybenzyloxy)methyl)-2,2-dimethyl-4-(5-methyl-3-oxohex-1-ynyl)oxazolidine-3-carboxylate

: 1437250-06-0
(4R,5S)-tert-butyl 4-((S)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1437250-09-3
(4R,5S)-tert-butyl 4-((R)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: With (R)-(+)-2-methyl-CBS-oxazaborolidine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; at -60 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ol401110x

Reference yield:

: 1437250-03-7
(4S,5R)-tert-butyl 4-ethynyl-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

: 590-86-3
isovaleraldehyde

: 1437250-06-0
(4R,5S)-tert-butyl 4-((S)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1437250-09-3
(4R,5S)-tert-butyl 4-((R)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: (4S,5R)-tert-butyl 4-ethynyl-5-((4-methoxybenzyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.75h; Inert atmosphere;

isovaleraldehyde; In tetrahydrofuran; hexane; at -100 ℃; for 3h; Overall yield = 67%; Overall yield = 236 mg;
DOI:10.1021/ol401110x

Reference yield:

: 1437249-97-2
(4R,5S)-3-tert-butyl 5-methyl 4-ethynyl-2,2-dimethyloxazolidine-3,5-dicarboxylate

: 1437250-09-3
(4R,5S)-tert-butyl 4-((R)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

2.1: camphor-10-sulfonic acid / dichloromethane / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -100 °C / Inert atmosphere

3.2: 3 h / -100 °C

With lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol401110x