(2S,5R)-6-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-5-hydroxyheptanoic acid

Base Information

Chemical Name:(2S,5R)-6-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-5-hydroxyheptanoic acid
CAS No.:96359-88-5
Molecular Formula:C₁₉H₂₈N₂O₇
Molecular Weight:396.441
Hs Code.:

Synonyms:(2S,5R)-6-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-5-hydroxyheptanoic acid

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Chemical Property of (2S,5R)-6-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-5-hydroxyheptanoic acid

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Technology Process of (2S,5R)-6-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-5-hydroxyheptanoic acid

There total 17 articles about (2S,5R)-6-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-5-hydroxyheptanoic acid 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: 76.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 79432-14-7
(2S,5R)-2-amino-6-[(benzyloxycarbonyl)amino]-5-hydroxyhexanoic acid

: 96359-88-5
(2S,5R)-6-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-5-hydroxyheptanoic acid

Guidance literature:: With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1016/S0957-4166(00)00195-6

Reference yield:

: 144090-57-3
tert-butyl (S)-4-(but-3-enyl)-2,2-dimethyloxazolidine-3-carboxylate

: 96359-88-5
(2S,5S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-5-hydroxy-hexanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / m-chloroperbenzoic acid (mCPBA) / 1,2-dichloro-ethane; H₂O / 50 °C / pH 8

2: 48 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol; H₂O / 50 °C

3: 97 percent / NaH, n-Bu₄NI / tetrahydrofuran / Ambient temperature

4: 99 percent / TsOH / methanol / Ambient temperature

5: CrO₃, dil. H₂SO₄ / acetone / 0 °C

6: H₂, dil. HCl / 20percent Pd(OH)2 / ethanol

7: aq. NaOH / ethanol; tetrahydrofuran

With chromium(VI) oxide; hydrogenchloride; sodium hydroxide; sodium azide; sulfuric acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; 2-methoxy-ethanol; water; 1,2-dichloro-ethane; acetone;
DOI:10.1039/c39920001064

Reference yield:

: 144090-58-4,144090-70-0
(S)-2,2-Dimethyl-4-(2-oxiranyl-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester

: 96359-88-5
(2S,5R)-6-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-5-hydroxyheptanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 48 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol; H₂O / 50 °C

2: 97 percent / NaH, n-Bu₄NI / tetrahydrofuran / Ambient temperature

3: TsOH / methanol / Ambient temperature

4: CrO₃, dil. H₂SO₄ / acetone / 0 °C

5: H₂, dil. HCl / 20percent Pd(OH)2 / ethanol

6: aq. NaOH / ethanol; tetrahydrofuran

With chromium(VI) oxide; hydrogenchloride; sodium hydroxide; sodium azide; sulfuric acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; 2-methoxy-ethanol; water; acetone;
DOI:10.1039/c39920001064