(3aR,4R,7R,7aR)-5-(4'-but-2'-ynyloxybenzenesulfonyl)-7-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid hydroxy amide

Base Information

Chemical Name:(3aR,4R,7R,7aR)-5-(4'-but-2'-ynyloxybenzenesulfonyl)-7-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid hydroxy amide
CAS No.:683210-73-3
Molecular Formula:C₁₉H₂₄N₂O₈S
Molecular Weight:440.474
Hs Code.:

Synonyms:(3aR,4R,7R,7aR)-5-(4'-but-2'-ynyloxybenzenesulfonyl)-7-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid hydroxy amide

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Chemical Property of (3aR,4R,7R,7aR)-5-(4'-but-2'-ynyloxybenzenesulfonyl)-7-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid hydroxy amide

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Technology Process of (3aR,4R,7R,7aR)-5-(4'-but-2'-ynyloxybenzenesulfonyl)-7-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid hydroxy amide

There total 6 articles about (3aR,4R,7R,7aR)-5-(4'-but-2'-ynyloxybenzenesulfonyl)-7-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid hydroxy amide 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: 35.0%

: 683210-70-0
(3aR,4R,7R,7aR)-5-(4'-but-2'-ynyloxybenzenesulfonyl)-7-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid methyl ester

: 683210-73-3
(3aR,4R,7R,7aR)-5-(4'-but-2'-ynyloxybenzenesulfonyl)-7-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid hydroxy amide

Guidance literature:: With sodium cyanide; hydroxylamine; In methanol; at 20 ℃;
DOI:10.1021/jm0304313

Reference yield:

: 87001-32-9
p-benzyloxybenzenesulfonyl chloride

: 683210-73-3
(3aR,4R,7R,7aR)-5-(4'-but-2'-ynyloxybenzenesulfonyl)-7-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid hydroxy amide

Guidance literature:: Multi-step reaction with 7 steps

1: 4-DMAP / dimethylformamide

2: cerium chloride heptahydrate; oxalic acid / acetonitrile / 1.17 h / 20 °C

3: 86 percent / triethylamine / CH₂Cl₂ / 1 h / -40 °C

4: 72 percent / potassium carbonate / dimethylformamide / 1.17 h / 45 °C

5: H₂ / Pd/C / ethyl acetate / 2 h / 40 °C / 2280 Torr

6: 4.4 g / potassium carbonate / acetonitrile / 0.5 h / 90 °C

7: 35 percent / aq. hydroxylamine; sodium cyanide / methanol / 20 °C

With dmap; sodium cyanide; cerium(III) chloride; hydrogen; hydroxylamine; oxalic acid; potassium carbonate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0304313

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

: 683210-73-3
(3aR,4R,7R,7aR)-5-(4'-but-2'-ynyloxybenzenesulfonyl)-7-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]-4-carboxylic acid hydroxy amide

Guidance literature:: Multi-step reaction with 7 steps

1: 4-DMAP / dimethylformamide

2: cerium chloride heptahydrate; oxalic acid / acetonitrile / 1.17 h / 20 °C

3: 86 percent / triethylamine / CH₂Cl₂ / 1 h / -40 °C

4: 72 percent / potassium carbonate / dimethylformamide / 1.17 h / 45 °C

5: H₂ / Pd/C / ethyl acetate / 2 h / 40 °C / 2280 Torr

6: 4.4 g / potassium carbonate / acetonitrile / 0.5 h / 90 °C

7: 35 percent / aq. hydroxylamine; sodium cyanide / methanol / 20 °C

With dmap; sodium cyanide; cerium(III) chloride; hydrogen; hydroxylamine; oxalic acid; potassium carbonate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0304313