(1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

Base Information

Chemical Name:(1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate
CAS No.:1370547-56-0
Molecular Formula:C₄₇H₆₉NO₉
Molecular Weight:792.066
Hs Code.:

(1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

Synonyms:(1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

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Chemical Property of (1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

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Technology Process of (1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

There total 16 articles about (1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate 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: 83.0%

: 1370547-53-7
(1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-6-oxo-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

: 1370547-56-0
(1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

Guidance literature:: With tert.-butylnitrite; In water; acetonitrile; at 28 - 35 ℃;
DOI:10.1021/jo300046v

Reference yield:

: enfumafungine

: 1370547-56-0
(1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

Guidance literature:: Multi-step reaction with 12 steps

1: triethylsilane; trifluoroacetic acid / dichloromethane / 1.08 h / 20 - 30 °C

2: sulfuric acid / 14 h / Reflux; Large scale reaction

3: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 25 - 78 °C / Large scale reaction

4: potassium 2-methylbutan-2-olate / N,N-dimethyl acetamide; toluene / 24.5 h / 20 - 25 °C / Large scale reaction

5: toluene-4-sulfonic acid; acetic acid / Isopropyl acetate / 3.5 h / 20 - 60 °C / Large scale reaction

6: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran / 0.5 h / 50 °C / Large scale reaction

7: potassium carbonate / tetrahydrofuran; toluene / 3 h / 20 °C

8: sodium hydroxide / 6 h / 20 °C / Large scale reaction

9: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 35 °C / Large scale reaction

10: ammonia / toluene / 24 h / -10 - 40 °C / 9826.07 Torr / Large scale reaction

11: 20 % Pd(OH)2/C; potassium carbonate / dichloromethane / 31 h / 20 °C

12: tert.-butylnitrite / water; acetonitrile / 28 - 35 °C

With triethylsilane; formic acid; tert.-butylnitrite; sulfuric acid; palladium 10% on activated carbon; 20 % Pd(OH)2/C; ammonia; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; Isopropyl acetate; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo300046v

Reference yield:

: 952577-51-4
(S)-2-ethoxycarbonylamino-2,3-dimethylbutyric acid

: 1370547-56-0
(1S,2R,3R,4aR,6R,6aS,7R,8R,10aR,10bR,12aR)-2-((S)-2-(((benzyloxy)carbonyl)(methyl)amino)-2,3-dimethylbutoxy)-6-(tert-butylperoxy)-7-carbamoyl-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysen-3-yl acetate

Guidance literature:: Multi-step reaction with 12 steps

1: lithium aluminium tetrahydride / tetrahydrofuran; 2-methyltetrahydrofuran / 60 °C / Large scale reaction

2: thionyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / -17 - -3 °C / Large scale reaction

3: sodium periodate; rhodium(III) chloride hydrate / acetonitrile / 20 °C / Large scale reaction

4: potassium 2-methylbutan-2-olate / N,N-dimethyl acetamide; toluene / 24.5 h / 20 - 25 °C / Large scale reaction

5: toluene-4-sulfonic acid; acetic acid / Isopropyl acetate / 3.5 h / 20 - 60 °C / Large scale reaction

6: palladium 10% on activated carbon; formic acid; triethylamine / tetrahydrofuran / 0.5 h / 50 °C / Large scale reaction

7: potassium carbonate / tetrahydrofuran; toluene / 3 h / 20 °C

8: sodium hydroxide / 6 h / 20 °C / Large scale reaction

9: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 35 °C / Large scale reaction

10: ammonia / toluene / 24 h / -10 - 40 °C / 9826.07 Torr / Large scale reaction

11: 20 % Pd(OH)2/C; potassium carbonate / dichloromethane / 31 h / 20 °C

12: tert.-butylnitrite / water; acetonitrile / 28 - 35 °C

With sodium periodate; lithium aluminium tetrahydride; formic acid; thionyl chloride; tert.-butylnitrite; rhodium(III) chloride hydrate; palladium 10% on activated carbon; 20 % Pd(OH)2/C; ammonia; potassium 2-methylbutan-2-olate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; 2-methyltetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; Isopropyl acetate; water; toluene; acetonitrile;
DOI:10.1021/jo300046v