(1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Base Information

Chemical Name:(1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester
CAS No.:1026132-02-4
Molecular Formula:C₄₄H₅₈N₂O₈Si
Molecular Weight:771.039
Hs Code.:

(1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Synonyms:(1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

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Chemical Property of (1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

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Technology Process of (1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

There total 17 articles about (1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl 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:

: (E)-(S)-2-tert-Butoxycarbonylamino-hex-4-enoic acid

: 1026132-02-4
(1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 2,2,2-trifluoro-ethanol / 20 - 50 °C

2.1: t-BuOK; 4 Angstroem molecular sieves / tetrahydrofuran / 0 °C

3.1: aq. NaBH₄ / tetrahydrofuran

4.1: TBAF / tetrahydrofuran / 50 °C

5.1: pyridine

6.1: 51 percent / Cl₂Ru(-N(Mes)CH₂CH₂(Mes)N-)=CH-C₆H₄-O-i-Pr(o) / CH₂Cl₂ / Heating

7.1: 95 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

8.1: TMSOTf / CH₂Cl₂ / 0 °C

9.1: DMAP / acetonitrile

10.1: K₂CO₃ / methanol

11.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

12.1: dimethyldioxirane; Na₂SO₄ / -78 - 20 °C

12.2: 10-camphorsulfonic acid

13.1: NaBH₃CN; TFA / tetrahydrofuran / 0 °C

14.1: KOSiMe₃ / acetonitrile / 0 °C

15.1: acetonitrile / 50 °C

16.1: Dess-Martin periodinane / CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; potassium trimethylsilonate; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; sodium cyanoborohydride; potassium carbonate; Dess-Martin periodane; sodium sulfate; trifluoroacetic acid; Hoveyda-Grubbs Catalyst II; In tetrahydrofuran; methanol; dichloromethane; 2,2,2-trifluoroethanol; acetonitrile; 1.1: Ugi four-component condensation;
DOI:10.1039/b415030a

Reference yield:

: 2-but-2-enyl-4-[2-hydroxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-5-hydroxymethyl-3-oxo-3,4-dihydro-2H-pyrazine-1-carboxylic acid tert-butyl ester

: 1026132-02-4
(1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: pyridine

2.1: 51 percent / Cl₂Ru(-N(Mes)CH₂CH₂(Mes)N-)=CH-C₆H₄-O-i-Pr(o) / CH₂Cl₂ / Heating

3.1: 95 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

4.1: TMSOTf / CH₂Cl₂ / 0 °C

5.1: DMAP / acetonitrile

6.1: K₂CO₃ / methanol

7.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

8.1: dimethyldioxirane; Na₂SO₄ / -78 - 20 °C

8.2: 10-camphorsulfonic acid

9.1: NaBH₃CN; TFA / tetrahydrofuran / 0 °C

10.1: KOSiMe₃ / acetonitrile / 0 °C

11.1: acetonitrile / 50 °C

12.1: Dess-Martin periodinane / CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; dmap; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; potassium trimethylsilonate; 3,3-dimethyldioxirane; sodium cyanoborohydride; potassium carbonate; Dess-Martin periodane; sodium sulfate; trifluoroacetic acid; Hoveyda-Grubbs Catalyst II; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1039/b415030a

Reference yield:

: 847671-87-8
4-[2-acetoxy-1-(2-methanesulfonyloxy-3,5-dimethoxy-4-methyl-phenyl)-ethyl]-5-acetoxymethyl-2-but-2-enyl-3-oxo-3,4-dihydro-2H-pyrazine-1-carboxylic acid tert-butyl ester

: 1026132-02-4
(1S,4R,5R,6S)-3-[(R)-1-(2-Benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-2-triisopropylsilanyloxy-ethyl]-4-formyl-2-oxo-6-vinyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 51 percent / Cl₂Ru(-N(Mes)CH₂CH₂(Mes)N-)=CH-C₆H₄-O-i-Pr(o) / CH₂Cl₂ / Heating

2.1: 95 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

3.1: TMSOTf / CH₂Cl₂ / 0 °C

4.1: DMAP / acetonitrile

5.1: K₂CO₃ / methanol

6.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

7.1: dimethyldioxirane; Na₂SO₄ / -78 - 20 °C

7.2: 10-camphorsulfonic acid

8.1: NaBH₃CN; TFA / tetrahydrofuran / 0 °C

9.1: KOSiMe₃ / acetonitrile / 0 °C

10.1: acetonitrile / 50 °C

11.1: Dess-Martin periodinane / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; potassium trimethylsilonate; 3,3-dimethyldioxirane; sodium cyanoborohydride; potassium carbonate; Dess-Martin periodane; sodium sulfate; trifluoroacetic acid; Hoveyda-Grubbs Catalyst II; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1039/b415030a