(+)-4-bromo-N-{(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-[(5-methyl-2-furyl)methyl]ethyl}-N-prop-2-ynylbenzenesulfonamide

Base Information

Chemical Name:(+)-4-bromo-N-{(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-[(5-methyl-2-furyl)methyl]ethyl}-N-prop-2-ynylbenzenesulfonamide
CAS No.:904682-16-2
Molecular Formula:C₂₃H₃₂BrNO₄SSi
Molecular Weight:526.567
Hs Code.:

Synonyms:(+)-4-bromo-N-{(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-[(5-methyl-2-furyl)methyl]ethyl}-N-prop-2-ynylbenzenesulfonamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-4-bromo-N-{(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-[(5-methyl-2-furyl)methyl]ethyl}-N-prop-2-ynylbenzenesulfonamide

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Technology Process of (+)-4-bromo-N-{(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-[(5-methyl-2-furyl)methyl]ethyl}-N-prop-2-ynylbenzenesulfonamide

There total 7 articles about (+)-4-bromo-N-{(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-[(5-methyl-2-furyl)methyl]ethyl}-N-prop-2-ynylbenzenesulfonamide 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: 66.0%

: 904682-14-0
(+)-4-bromo-N-{(1R)-2-hydroxy-1-[(5-methyl-2-furyl)methyl]ethyl}-N-prop-2-ynylbenzenesulfonamide

: 18162-48-6
tert-butyldimethylsilyl chloride

: 904682-16-2
(+)-4-bromo-N-{(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-[(5-methyl-2-furyl)methyl]ethyl}-N-prop-2-ynylbenzenesulfonamide

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1002/chem.200600192

Reference yield:

: 620-02-0
5-Methylfurfural

: 904682-16-2
(+)-4-bromo-N-{(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-[(5-methyl-2-furyl)methyl]ethyl}-N-prop-2-ynylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 7 steps

1: 71 percent / t-BuOK / CH₂Cl₂ / 2 h / 20 °C

2: 98 percent / MandyPhos(OMe); H₂ / [Rh(nbd)2]BF₄ / methanol; toluene / 16.5 h / 20 °C / 3750.38 Torr

3: cyclohexene / Pd/C / methanol / 1 h / Heating

4: 1.22 g / Et₃N / CH₂Cl₂ / 0 - 20 °C

5: 88 percent / DIBALH / tetrahydrofuran; hexane / -78 - 20 °C

6: 81 percent / Cs₂CO₃ / acetone; toluene / 20 °C

7: 66 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; caesium carbonate; triethylamine; cyclohexene; palladium on activated charcoal; di(norbornadiene)rhodium(I) tetrafluoroborate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/chem.200600192

Reference yield:

: 226880-87-1
methyl (2R)-(-)-2-benzyloxycarbonylamino-3-(5-methylfuran-2-yl)propanoate

: 904682-16-2
(+)-4-bromo-N-{(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-[(5-methyl-2-furyl)methyl]ethyl}-N-prop-2-ynylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1: cyclohexene / Pd/C / methanol / 1 h / Heating

2: 1.22 g / Et₃N / CH₂Cl₂ / 0 - 20 °C

3: 88 percent / DIBALH / tetrahydrofuran; hexane / -78 - 20 °C

4: 81 percent / Cs₂CO₃ / acetone; toluene / 20 °C

5: 66 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; diisobutylaluminium hydride; caesium carbonate; triethylamine; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/chem.200600192