(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

Base Information

Chemical Name:(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
CAS No.:1309358-12-0
Molecular Formula:C₃₃H₄₉NO₈Si
Molecular Weight:615.839
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 85.0%

: 1309358-11-9
(3S,4R,5R,2'S,3'S)-3,4-(2',3'-dimethoxy-butylene-2',3'-dioxy)-2-hydroxy-5-hydroxymethyl-1-(tert-butyloxycarbonyl)piperidine

: 58479-61-1
tert-butylchlorodiphenylsilane

: 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

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3.16h; Inert atmosphere;
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

: 1309358-12-0
(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

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol200942g

Reference yield:

: C₂₁H₂₉NO₁₀

: 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

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; acetic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol200942g