(3aS,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-oxo-5-(toluene-4-sulfonyl)-hexahydro[1,3]dioxolo[4,5-c]-pyridine-6-carboxylic acid

Base Information

Chemical Name:(3aS,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-oxo-5-(toluene-4-sulfonyl)-hexahydro[1,3]dioxolo[4,5-c]-pyridine-6-carboxylic acid
CAS No.:479411-13-7
Molecular Formula:C₂₃H₂₅NO₈S
Molecular Weight:475.519
Hs Code.:

Synonyms:(3aS,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-oxo-5-(toluene-4-sulfonyl)-hexahydro[1,3]dioxolo[4,5-c]-pyridine-6-carboxylic acid

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Chemical Property of (3aS,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-oxo-5-(toluene-4-sulfonyl)-hexahydro[1,3]dioxolo[4,5-c]-pyridine-6-carboxylic acid

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Technology Process of (3aS,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-oxo-5-(toluene-4-sulfonyl)-hexahydro[1,3]dioxolo[4,5-c]-pyridine-6-carboxylic acid

There total 14 articles about (3aS,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-oxo-5-(toluene-4-sulfonyl)-hexahydro[1,3]dioxolo[4,5-c]-pyridine-6-carboxylic acid 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: 85.0%

: 479411-12-6
(3aS,6R,7R,7aS)-7-benzyloxy-6-hydroxymethyl-2,2-dimethyl-5-(toluene-4-sulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]-pyridine-4-one

: 479411-13-7
(3aS,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-oxo-5-(toluene-4-sulfonyl)-hexahydro[1,3]dioxolo[4,5-c]-pyridine-6-carboxylic acid

Guidance literature:: With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; for 2h;
DOI:10.1016/S0040-4020(02)00674-9

Reference yield:

: 222986-35-8
(1R)-2-[(tert-butyldimethylsilyl)oxy]-1-(furan-2-yl)ethanol

: 479411-13-7
(3aS,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-oxo-5-(toluene-4-sulfonyl)-hexahydro[1,3]dioxolo[4,5-c]-pyridine-6-carboxylic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: 80 percent / diphenylphosphorazide; DBU / toluene / 10 h

2.1: hydrogen / 10 percent Pd/C / ethyl acetate / 0.67 h / 750.06 Torr

3.1: 2.57 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

4.1: 92 percent / m-chloroperbenzoic acide / CH₂Cl₂ / 4 h / 20 °C

5.1: 94 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / tetrahydrofuran / 3 h / 0 °C

6.1: 89 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.67 h / -30 °C

7.1: sodium hydride / tetrahydrofuran / 0.5 h

7.2: 91 percent / Bu₄NI / tetrahydrofuran / 2 h

8.1: 93 percent / 4 Angstroem molecular sieves; m-chloroperbenzoic acid; BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

9.1: 96 percent / 4-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; acetone / 6 h

10.1: 90 percent / p-TsOH / acetone / 5 h

11.1: 92 percent / TBAF / tetrahydrofuran / 2 h

12.1: 85 percent / NaIO₄; RuCl₃ / H₂O; CCl₄; acetonitrile / 2 h

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; 4 A molecular sieve; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4020(02)00674-9

Reference yield:

: (S)-(2-azido-2-furan-2-yl-ethoxy)-tert-butyl-dimethyl-silane

: 479411-13-7
(3aS,6R,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-oxo-5-(toluene-4-sulfonyl)-hexahydro[1,3]dioxolo[4,5-c]-pyridine-6-carboxylic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: hydrogen / 10 percent Pd/C / ethyl acetate / 0.67 h / 750.06 Torr

2.1: 2.57 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

3.1: 92 percent / m-chloroperbenzoic acide / CH₂Cl₂ / 4 h / 20 °C

4.1: 94 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / tetrahydrofuran / 3 h / 0 °C

5.1: 89 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.67 h / -30 °C

6.1: sodium hydride / tetrahydrofuran / 0.5 h

6.2: 91 percent / Bu₄NI / tetrahydrofuran / 2 h

7.1: 93 percent / 4 Angstroem molecular sieves; m-chloroperbenzoic acid; BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

8.1: 96 percent / 4-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; acetone / 6 h

9.1: 90 percent / p-TsOH / acetone / 5 h

10.1: 92 percent / TBAF / tetrahydrofuran / 2 h

11.1: 85 percent / NaIO₄; RuCl₃ / H₂O; CCl₄; acetonitrile / 2 h

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4020(02)00674-9