(S)-2-((2S,3S,4S)-2-Benzylamino-5-carbamoyloxy-3,4-dihydroxy-pentanoylamino)-4-methyl-pentanoic acid benzyl ester

Base Information

Chemical Name:(S)-2-((2S,3S,4S)-2-Benzylamino-5-carbamoyloxy-3,4-dihydroxy-pentanoylamino)-4-methyl-pentanoic acid benzyl ester
CAS No.:213480-31-0
Molecular Formula:C₂₆H₃₅N₃O₇
Molecular Weight:501.58
Hs Code.:

Synonyms:(S)-2-((2S,3S,4S)-2-Benzylamino-5-carbamoyloxy-3,4-dihydroxy-pentanoylamino)-4-methyl-pentanoic acid benzyl ester

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Chemical Property of (S)-2-((2S,3S,4S)-2-Benzylamino-5-carbamoyloxy-3,4-dihydroxy-pentanoylamino)-4-methyl-pentanoic acid benzyl ester

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Technology Process of (S)-2-((2S,3S,4S)-2-Benzylamino-5-carbamoyloxy-3,4-dihydroxy-pentanoylamino)-4-methyl-pentanoic acid benzyl ester

There total 7 articles about (S)-2-((2S,3S,4S)-2-Benzylamino-5-carbamoyloxy-3,4-dihydroxy-pentanoylamino)-4-methyl-pentanoic acid benzyl ester 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:

: 190007-79-5
(3R,4S)-1-benzyl-4-[(1S,5S)-5-benzyloxymethyl-3,3-dimethyl-2,4-dioxacyclopentane-1-yl]-3-benzyloxyazetidin-2-one

: 213480-31-0
(S)-2-((2S,3S,4S)-2-Benzylamino-5-carbamoyloxy-3,4-dihydroxy-pentanoylamino)-4-methyl-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / hydrogen / Pd/C / methanol / 20 °C / 760 Torr

2: pyridine / CH₂Cl₂ / 0.75 h / 0 - 20 °C

3: 9.95 g / aq. NH₃ / tetrahydrofuran / 0.5 h / 0 - 20 °C

4: 91 percent / hydrogen / Pd/C / methanol / 16 h / 20 °C / 760 Torr

5: 90 percent / sodium hypochlorite; 2,2,6,6-tetramethylpiperidin-1-oxyl; potassium bromide / CH₂Cl₂; aq. phosphate buffer / -5 - 0 °C / pH 7

6: 87 percent / CH₂Cl₂ / 24 h / 20 °C

7: TFA / methanol

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; ammonium hydroxide; sodium hypochlorite; hydrogen; trifluoroacetic acid; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; 1: Hydrogenolysis / 2: Esterification / 3: ammonolysis / 4: Hydrogenolysis / 5: Oxidation / 6: Condensation / 7: Ring cleavage;
DOI:10.1021/jo980354x

Reference yield:

: 213480-20-7
(3R,4S)-1-Benzyl-3-benzyloxy-4-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-azetidin-2-one

: 213480-31-0
(S)-2-((2S,3S,4S)-2-Benzylamino-5-carbamoyloxy-3,4-dihydroxy-pentanoylamino)-4-methyl-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / CH₂Cl₂ / 0.75 h / 0 - 20 °C

2: 9.95 g / aq. NH₃ / tetrahydrofuran / 0.5 h / 0 - 20 °C

3: 91 percent / hydrogen / Pd/C / methanol / 16 h / 20 °C / 760 Torr

4: 90 percent / sodium hypochlorite; 2,2,6,6-tetramethylpiperidin-1-oxyl; potassium bromide / CH₂Cl₂; aq. phosphate buffer / -5 - 0 °C / pH 7

5: 87 percent / CH₂Cl₂ / 24 h / 20 °C

6: TFA / methanol

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; ammonium hydroxide; sodium hypochlorite; hydrogen; trifluoroacetic acid; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; 1: Esterification / 2: ammonolysis / 3: Hydrogenolysis / 4: Oxidation / 5: Condensation / 6: Ring cleavage;
DOI:10.1021/jo980354x

Reference yield:

: 213480-21-8
Carbamic acid (4S,5S)-5-((2S,3R)-1-benzyl-3-benzyloxy-4-oxo-azetidin-2-yl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

: 213480-31-0
(S)-2-((2S,3S,4S)-2-Benzylamino-5-carbamoyloxy-3,4-dihydroxy-pentanoylamino)-4-methyl-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / hydrogen / Pd/C / methanol / 16 h / 20 °C / 760 Torr

2: 90 percent / sodium hypochlorite; 2,2,6,6-tetramethylpiperidin-1-oxyl; potassium bromide / CH₂Cl₂; aq. phosphate buffer / -5 - 0 °C / pH 7

3: 87 percent / CH₂Cl₂ / 24 h / 20 °C

4: TFA / methanol

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; hydrogen; trifluoroacetic acid; potassium bromide; palladium on activated charcoal; In methanol; phosphate buffer; dichloromethane; 1: Hydrogenolysis / 2: Oxidation / 3: Condensation / 4: Ring cleavage;
DOI:10.1021/jo980354x