(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1-hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1-hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:640773-16-6
Molecular Formula:C₂₆H₄₃NO₉SSi
Molecular Weight:573.78
Hs Code.:

(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1-hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-carboxylic acid benzyl ester

Synonyms:(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1-hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1-hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1-hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-carboxylic acid benzyl ester

There total 6 articles about (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1-hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-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: 86.0%

: 124-63-0
methanesulfonyl chloride

: 640773-12-2
(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-carboxylic acid benzyl ester

: 640773-16-6
(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1-hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: With triethylamine; In dichloromethane; at -40 ℃; for 0.0833333h;
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

: 640773-16-6
(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1-hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 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: 86 percent / Et₃N / CH₂Cl₂ / 0.08 h / -40 °C

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

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 640773-16-6
(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(4R,5R)-5-((R)-1-hydroxy-2-methanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / imidazole / dimethylformamide / 6 h / 20 °C

2.1: O₃ / methanol / -78 °C

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

3.1: 1.01 g / H₂ / Pd(OH)2/C / ethanol / 10 h / 20 °C

4.1: 90 percent / aq. K₂CO₃ / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 93 percent / Dowex 50W-X₈ / aq. methanol / 18 h / 20 °C

6.1: 86 percent / Et₃N / CH₂Cl₂ / 0.08 h / -40 °C

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