(S)-2-{(S)-2-[2-((3aS,4S,6S,6aS)-6-tert-Butoxycarbonylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

Base Information

Chemical Name:(S)-2-{(S)-2-[2-((3aS,4S,6S,6aS)-6-tert-Butoxycarbonylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester
CAS No.:578764-46-2
Molecular Formula:C₃₀H₄₅N₃O₉
Molecular Weight:591.702
Hs Code.:

(S)-2-{(S)-2-[2-((3aS,4S,6S,6aS)-6-tert-Butoxycarbonylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

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Chemical Property of (S)-2-{(S)-2-[2-((3aS,4S,6S,6aS)-6-tert-Butoxycarbonylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

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Technology Process of (S)-2-{(S)-2-[2-((3aS,4S,6S,6aS)-6-tert-Butoxycarbonylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

There total 5 articles about (S)-2-{(S)-2-[2-((3aS,4S,6S,6aS)-6-tert-Butoxycarbonylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl 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:

: 55036-19-6
methyl [(3aS,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]acetate

: 578764-46-2
(S)-2-{(S)-2-[2-((3aS,4S,6S,6aS)-6-tert-Butoxycarbonylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / TEMPO; KBr; (nBu)4NCl / NaHCO₃; NaOCl / CH₂Cl₂; H₂O

2: 64 percent / 4A MS; diphenylphosphorazidate; Et₃N / 16 h / 80 °C

3: 63 percent / LiOH; H₂O₂ / tetrahydrofuran / 3 h / 0 °C

4: 0.32 g / HOBt; EDC*HCl; NMM / dimethylformamide / 16 h / 20 °C

With 4-methyl-morpholine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; diphenyl phosphoryl azide; tetrabutyl-ammonium chloride; dihydrogen peroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 2: Curtius rearrangement;
DOI:10.1002/ejoc.200210682

Reference yield:

: 38155-19-0
L-phenylalanyl-L-leucine methyl ester

: 578764-41-7
3,6-anhydro-6-(tert-butoxycarbonylamino)-2,6-dideoxy-4,5-O-isopropylidene-D-allo-hexonoic acid

: 578764-46-2
(S)-2-{(S)-2-[2-((3aS,4S,6S,6aS)-6-tert-Butoxycarbonylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

Guidance literature:: With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1002/ejoc.200210682

Reference yield:

: 64152-76-7
methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-4-methylpentanoate

: 578764-46-2
(S)-2-{(S)-2-[2-((3aS,4S,6S,6aS)-6-tert-Butoxycarbonylamino-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 0.08 h

2: 0.32 g / HOBt; EDC*HCl; NMM / dimethylformamide / 16 h / 20 °C

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200210682