(3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxymethyl)-1-(tert-butyloxycarbonyl)piperidin-2-one

Base Information

Chemical Name:(3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxymethyl)-1-(tert-butyloxycarbonyl)piperidin-2-one
CAS No.:1309358-13-1
Molecular Formula:C₃₃H₄₇NO₈Si
Molecular Weight:613.824
Hs Code.:

Synonyms:(3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxymethyl)-1-(tert-butyloxycarbonyl)piperidin-2-one

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Chemical Property of (3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxymethyl)-1-(tert-butyloxycarbonyl)piperidin-2-one

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Technology Process of (3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxymethyl)-1-(tert-butyloxycarbonyl)piperidin-2-one

There total 8 articles about (3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxymethyl)-1-(tert-butyloxycarbonyl)piperidin-2-one 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: 81.0%

: 1309358-12-0
(3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-2-hydroxy-5-(tert-butyldiphenylsilyloxymethyl)-1-(tert-butyloxycarbonyl)piperidine

: 1309358-13-1
(3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxymethyl)-1-(tert-butyloxycarbonyl)piperidin-2-one

Guidance literature:: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/ol200942g

Reference yield:

: benzyl(2'S,3'S)-2,3-O-[2',3'-dimethoxybutane-2',3'-diyl]-4-C-nitromethyl-α-L-xylopyranoside

: 1309358-13-1
(3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxymethyl)-1-(tert-butyloxycarbonyl)piperidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: toluene-4-sulfonic acid / 7 h / 20 °C / Inert atmosphere

2: sodium tetrahydroborate / ethanol / 0 - 20 °C

3: lithium aluminium tetrahydride / tetrahydrofuran / 18.16 h / 0 - 20 °C / Inert atmosphere

4: triethylamine / dichloromethane / 20 °C

5: palladium 10% on activated carbon; hydrogen; acetic acid / ethyl acetate / 24 h / 20 °C / 760.05 Torr

6: 1H-imidazole / N,N-dimethyl-formamide / 3.16 h / 0 - 20 °C / Inert atmosphere

7: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; toluene-4-sulfonic acid; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol200942g

Reference yield:

: C₂₁H₂₉NO₁₀

: 1309358-13-1
(3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxymethyl)-1-(tert-butyloxycarbonyl)piperidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: sodium tetrahydroborate / ethanol / 0 - 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 18.16 h / 0 - 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 20 °C

4: palladium 10% on activated carbon; hydrogen; acetic acid / ethyl acetate / 24 h / 20 °C / 760.05 Torr

5: 1H-imidazole / N,N-dimethyl-formamide / 3.16 h / 0 - 20 °C / Inert atmosphere

6: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol200942g