(4R)-N-6-[(benzyloxy)carbonyl]-N-2-(tert-butoxycarbonyl)-4-fluoro-3-methyl-L-lysine

Base Information

Chemical Name:(4R)-N-6-[(benzyloxy)carbonyl]-N-2-(tert-butoxycarbonyl)-4-fluoro-3-methyl-L-lysine
CAS No.:650604-80-1
Molecular Formula:C₁₉H₂₇FN₂O₆
Molecular Weight:398.432
Hs Code.:

Synonyms:(4R)-N-6-[(benzyloxy)carbonyl]-N-2-(tert-butoxycarbonyl)-4-fluoro-3-methyl-L-lysine

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Chemical Property of (4R)-N-6-[(benzyloxy)carbonyl]-N-2-(tert-butoxycarbonyl)-4-fluoro-3-methyl-L-lysine

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Technology Process of (4R)-N-6-[(benzyloxy)carbonyl]-N-2-(tert-butoxycarbonyl)-4-fluoro-3-methyl-L-lysine

There total 10 articles about (4R)-N-6-[(benzyloxy)carbonyl]-N-2-(tert-butoxycarbonyl)-4-fluoro-3-methyl-L-lysine 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: 77.0%

: 650604-79-8
phenylmethyl [(3R,5S)-5-[[(1,1-dimethylethoxy)carbonyl]amino]-3-fluoro-6-hydroxyhexyl]carbamate

: 650604-80-1
(4R)-N-6-[(benzyloxy)carbonyl]-N-2-(tert-butoxycarbonyl)-4-fluoro-3-methyl-L-lysine

Guidance literature:: With ruthenium trichloride; sodium periodate; In acetonitrile; at 20 ℃; for 2.5h;
DOI:10.1039/b307563j

Reference yield:

: 95715-87-0
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

: 650604-80-1
(4R)-N-6-[(benzyloxy)carbonyl]-N-2-(tert-butoxycarbonyl)-4-fluoro-3-methyl-L-lysine

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 18 h / 20 °C

1.2: tetrahydrofuran / 5 h / 5 - 20 °C

1.3: 85 percent / tetrahydrofuran / 18 h

2.1: 100 percent / H₂ / Pd/C / ethanol / 18 h / 20 °C / 3102.97 Torr

3.1: NaBH₄ / methanol / -50 - 0 °C

4.1: 99 percent / K₂CO₃ / tetrahydrofuran / 48 h / 20 °C

5.1: 99 percent / TEA; MsCl; DMAP / CH₂Cl₂ / 1 h / -70 °C

6.1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 3 h

7.1: 3.61 g / H₂ / Pd/C / ethanol / 24 h / 3102.97 Torr

8.1: 100 percent / aq. AcOH / 72 h / 20 °C

9.1: 66 percent / aq. KHCO₃ / acetone / 1 h / 20 °C

10.1: 77 percent / RuCl₃*H₂O; NaIO₄ / acetonitrile / 2.5 h / 20 °C

With dmap; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; TEA; hydrogen; sodium hydride; potassium carbonate; potassium hydrogencarbonate; acetic acid; methanesulfonyl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; acetonitrile; 1.2: Wadsworth-Emmons reaction / 1.3: Wadsworth-Emmons reaction / 4.1: Henry reaction;
DOI:10.1039/b307563j

Reference yield:

: 650604-76-5
tert-butyl (4S)-4-[(2S,3E)-2-fluoro-4-nitrobut-3-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 650604-80-1
(4R)-N-6-[(benzyloxy)carbonyl]-N-2-(tert-butoxycarbonyl)-4-fluoro-3-methyl-L-lysine

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 3 h

2: 3.61 g / H₂ / Pd/C / ethanol / 24 h / 3102.97 Torr

3: 100 percent / aq. AcOH / 72 h / 20 °C

4: 66 percent / aq. KHCO₃ / acetone / 1 h / 20 °C

5: 77 percent / RuCl₃*H₂O; NaIO₄ / acetonitrile / 2.5 h / 20 °C

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; hydrogen; potassium hydrogencarbonate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; acetone; acetonitrile;
DOI:10.1039/b307563j