tert-butyl (4R)-2,2-dimethyl-4-{(3E)-4-[(4R)-{2,2-dimethyl-3-([{benzyloxy}carbonyl]amino)}-1,3-oxazolidin-4-yl]-3-butenyl}-1,3-oxazolidine-3-carboxylate

Base Information

Chemical Name:tert-butyl (4R)-2,2-dimethyl-4-{(3E)-4-[(4R)-{2,2-dimethyl-3-([{benzyloxy}carbonyl]amino)}-1,3-oxazolidin-4-yl]-3-butenyl}-1,3-oxazolidine-3-carboxylate
CAS No.:412917-48-7
Molecular Formula:C₂₇H₄₀N₂O₆
Molecular Weight:488.624
Hs Code.:

Synonyms:tert-butyl (4R)-2,2-dimethyl-4-{(3E)-4-[(4R)-{2,2-dimethyl-3-([{benzyloxy}carbonyl]amino)}-1,3-oxazolidin-4-yl]-3-butenyl}-1,3-oxazolidine-3-carboxylate

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Chemical Property of tert-butyl (4R)-2,2-dimethyl-4-{(3E)-4-[(4R)-{2,2-dimethyl-3-([{benzyloxy}carbonyl]amino)}-1,3-oxazolidin-4-yl]-3-butenyl}-1,3-oxazolidine-3-carboxylate

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Technology Process of tert-butyl (4R)-2,2-dimethyl-4-{(3E)-4-[(4R)-{2,2-dimethyl-3-([{benzyloxy}carbonyl]amino)}-1,3-oxazolidin-4-yl]-3-butenyl}-1,3-oxazolidine-3-carboxylate

There total 5 articles about tert-butyl (4R)-2,2-dimethyl-4-{(3E)-4-[(4R)-{2,2-dimethyl-3-([{benzyloxy}carbonyl]amino)}-1,3-oxazolidin-4-yl]-3-butenyl}-1,3-oxazolidine-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: 67.0%

: 115378-31-9
tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate

: 412917-47-6
benzyl (4S)-4-[(E)-2-iodoethenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 412917-48-7
tert-butyl (4R)-2,2-dimethyl-4-{(3E)-4-[(4R)-{2,2-dimethyl-3-([{benzyloxy}carbonyl]amino)}-1,3-oxazolidin-4-yl]-3-butenyl}-1,3-oxazolidine-3-carboxylate

Guidance literature:: tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

benzyl (4S)-4-[(E)-2-iodoethenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate; With potassium phosphate; 1,1'-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride-chloroform adduct; In tetrahydrofuran; water; N,N-dimethyl-formamide; Further stages.;
DOI:10.1021/jo010865a

Reference yield:

: 1145-80-8
N-(benzyloxycarbonyl)-L-serine

: 412917-48-7
tert-butyl (4R)-2,2-dimethyl-4-{(3E)-4-[(4R)-{2,2-dimethyl-3-([{benzyloxy}carbonyl]amino)}-1,3-oxazolidin-4-yl]-3-butenyl}-1,3-oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-methylmorpholine; 1-(3-dimethylaminopopyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1 h / -15 °C

2.1: 29.6 percent / BF₃*OEt₂ / acetone / 2 h

3.1: LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

4.1: 56 percent / CrCl₂ / tetrahydrofuran / 3 h / -78 - 20 °C

5.1: 9-BBN-H / tetrahydrofuran / 2 h / 0 - 20 °C

5.2: 67 percent / K₃PO₄ / PdCl₂(dppf)*CHCl₃ / tetrahydrofuran; H₂O; dimethylformamide

With 4-methyl-morpholine; chromium dichloride; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; boron trifluoride diethyl etherate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; acetone; 5.2: Suzuki coupling;
DOI:10.1021/jo010865a

Reference yield:

: 117833-92-8
(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

: 412917-48-7
tert-butyl (4R)-2,2-dimethyl-4-{(3E)-4-[(4R)-{2,2-dimethyl-3-([{benzyloxy}carbonyl]amino)}-1,3-oxazolidin-4-yl]-3-butenyl}-1,3-oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 56 percent / CrCl₂ / tetrahydrofuran / 3 h / -78 - 20 °C

2.1: 9-BBN-H / tetrahydrofuran / 2 h / 0 - 20 °C

2.2: 67 percent / K₃PO₄ / PdCl₂(dppf)*CHCl₃ / tetrahydrofuran; H₂O; dimethylformamide

With chromium dichloride; 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; 2.2: Suzuki coupling;
DOI:10.1021/jo010865a