(1'R,2'S,3'S,3S)-2-(3',4'-anhydro-1',2'-O-isopropylidene-1',2'-dihydroxybutyl)-3-hydroxy-N-(benzyloxycarbonyl)-pyrrolidine

Base Information

Chemical Name:(1'R,2'S,3'S,3S)-2-(3',4'-anhydro-1',2'-O-isopropylidene-1',2'-dihydroxybutyl)-3-hydroxy-N-(benzyloxycarbonyl)-pyrrolidine
CAS No.:640773-15-5
Molecular Formula:C₁₉H₂₅NO₆
Molecular Weight:363.411
Hs Code.:

Synonyms:(1'R,2'S,3'S,3S)-2-(3',4'-anhydro-1',2'-O-isopropylidene-1',2'-dihydroxybutyl)-3-hydroxy-N-(benzyloxycarbonyl)-pyrrolidine

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Chemical Property of (1'R,2'S,3'S,3S)-2-(3',4'-anhydro-1',2'-O-isopropylidene-1',2'-dihydroxybutyl)-3-hydroxy-N-(benzyloxycarbonyl)-pyrrolidine

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Technology Process of (1'R,2'S,3'S,3S)-2-(3',4'-anhydro-1',2'-O-isopropylidene-1',2'-dihydroxybutyl)-3-hydroxy-N-(benzyloxycarbonyl)-pyrrolidine

There total 6 articles about (1'R,2'S,3'S,3S)-2-(3',4'-anhydro-1',2'-O-isopropylidene-1',2'-dihydroxybutyl)-3-hydroxy-N-(benzyloxycarbonyl)-pyrrolidine 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: 90.0%

: 640773-14-4
(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{(4R,5S)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methanesulfonyloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pyrrolidine-1-carboxylic acid benzyl ester

: 640773-15-5
(1'R,2'S,3'S,3S)-2-(3',4'-anhydro-1',2'-O-isopropylidene-1',2'-dihydroxybutyl)-3-hydroxy-N-(benzyloxycarbonyl)-pyrrolidine

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1055/s-2003-42423

Reference yield:

: 133473-13-9
2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannose

: 640773-15-5
(1'R,2'S,3'S,3S)-2-(3',4'-anhydro-1',2'-O-isopropylidene-1',2'-dihydroxybutyl)-3-hydroxy-N-(benzyloxycarbonyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1.1: In / tetrahydrofuran / Heating

1.2: (+)-cinchonine / tetrahydrofuran / 20 °C

1.3: 87 percent / tetrahydrofuran / 2 h / -78 °C

2.1: 98 percent / imidazole / dimethylformamide / 6 h / 20 °C

3.1: O₃ / methanol / -78 °C

3.2: Me₂S / methanol / 12 h / -78 - 20 °C

4.1: 1.01 g / H₂ / Pd(OH)2/C / ethanol / 10 h / 20 °C

5.1: 90 percent / aq. K₂CO₃ / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 93 percent / Dowex 50W-X₈ / aq. methanol / 18 h / 20 °C

7.1: 99 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

8.1: 92 percent / Et₃N / tetrahydrofuran / 0.33 h / 20 °C

9.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; indium; Dowex 50W-X₈; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; ozone; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2003-42423

Reference yield:

: 640773-09-7
(1S)-1-allyl-1-O-t-butyldimethylsilyl-2-[(9-phenylfluoren-9-yl)-amino]-2-deoxy-3,4;5,6-di-O-isopropylidene-D-mannitol

: 640773-15-5
(1'R,2'S,3'S,3S)-2-(3',4'-anhydro-1',2'-O-isopropylidene-1',2'-dihydroxybutyl)-3-hydroxy-N-(benzyloxycarbonyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: O₃ / methanol / -78 °C

1.2: Me₂S / methanol / 12 h / -78 - 20 °C

2.1: 1.01 g / H₂ / Pd(OH)2/C / ethanol / 10 h / 20 °C

3.1: 90 percent / aq. K₂CO₃ / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 93 percent / Dowex 50W-X₈ / aq. methanol / 18 h / 20 °C

5.1: 99 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

6.1: 92 percent / Et₃N / tetrahydrofuran / 0.33 h / 20 °C

7.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; Dowex 50W-X₈; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; ozone; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1055/s-2003-42423