(3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide

Base Information

Chemical Name:(3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide
CAS No.:642089-93-8
Molecular Formula:C₂₈H₃₀N₂O₈S
Molecular Weight:554.621
Hs Code.:

Synonyms:(3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide

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Chemical Property of (3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide

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Technology Process of (3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide

There total 9 articles about (3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide 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:

: 29601-98-7
N-benzylhydroxylamine hydrochloride

: (3aR,4R,7R,7aR)-7-Hydroxy-2,2-dimethyl-5-(4-phenoxy-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid

: 642089-93-8
(3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 2.5h;

Reference yield:

: (2R,4'S,4R,5'R)-azide-(2',2',2,2-tetramethyl-[4',4]bis[[1,3]dioxolanyl]-5'-yl)-acetic acid methyl ester

: 642089-93-8
(3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide

Guidance literature:: Multi-step reaction with 7 steps

1: H₂ / Pd/C / ethyl acetate / 4 h / 40 °C / 3040 Torr

2: 38.3 g / 4-DMAP / dimethylformamide / 20 °C

3: 67 percent / cerium chloride heptahydrate; oxalic acid / acetonitrile / 1.17 h / 20 °C

4: 46 percent / triethylamine / CH₂Cl₂ / 1 h / -40 °C

5: 92 percent / potassium carbonate / dimethylformamide / 1.17 h / 45 °C

6: aq. NaOH / methanol; dioxane / 1.17 h / 20 °C

7: 8.90 g / WSC; HOBt; DIEA / dimethylformamide / 20 °C

With dmap; sodium hydroxide; cerium(III) chloride; hydrogen; oxalic acid; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0304313

Reference yield:

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: (3aR,4R,7R,7aR)-7-Hydroxy-2,2-dimethyl-5-(4-phenoxy-benzenesulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid

: 642089-93-8
(3aR,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-5-(4'-phenoxybenzenesulfonyl)hexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid benzyloxyamide

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/jm0304313