(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

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 methyl ester
• CAS No.: 683210-70-0
• Molecular Formula: C₂₀H₂₅NO₈S
• Molecular Weight: 439.486
• Mol file: 683210-70-0.mol

Synonyms:(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

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 methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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 methyl ester

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 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:

1-Bromo-2-butyne (3355-28-0) + (3aR,4R,7R,7aR)-7-Hydroxy-5-(4-hydroxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid methyl ester → (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 (683210-70-0)

Guidance literature:

With potassium carbonate; In acetonitrile; at 90 ℃; for 0.5h;

DOI:10.1021/jm0304313

Reference yield:

p-benzyloxybenzenesulfonyl chloride (87001-32-9) → (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 (683210-70-0)

Guidance literature:

Multi-step reaction with 6 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

With dmap; cerium(III) chloride; hydrogen; oxalic acid; potassium carbonate; triethylamine; palladium on activated charcoal; In 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 → (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 (683210-70-0)

Guidance literature:

Multi-step reaction with 6 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

With dmap; cerium(III) chloride; hydrogen; oxalic acid; potassium carbonate; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm0304313

upstream raw materials:

1-Bromo-2-butyne

p-benzyloxybenzenesulfonyl chloride

(1,2R,4'R,5'S)-(4-benzyloxybenzenesulfonylamino)-[5'-(1,2-dihydroxyethyl)-2',2-dimethyl[1,3]-dioxolan-4'-yl]acetic acid methyl ester

(1S,2R,4'R,5'S)-(benzyloxybenzenesulfonylamino)-[5'-(1-hydroxy-2-methanesulfonyloxyethyl)-2',2'-dimethyl[1,3]dioxolan-4'-yl]acetic acid methyl ester

Downstream raw materials:

(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