(2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanenitrile

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Chemical Name:(2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanenitrile
CAS No.:1309358-16-4
Molecular Formula:C₃₃H₄₈N₂O₇Si
Molecular Weight:612.839
Hs Code.:

Synonyms:(2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanenitrile

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Chemical Property of (2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanenitrile

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Technology Process of (2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanenitrile

There total 10 articles about (2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanenitrile 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: 91.0%

: 1309358-15-3
(2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanamide

: 1309358-16-4
(2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanenitrile

Guidance literature:: (2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanamide; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1.5h;

With benzyl(2'S,3'S)-2,3-O-[2',3'-dimethoxybutane-2',3'-diyl]-4-C-nitromethyl-α-L-xylopyranoside; In dichloromethane; at -78 - 20 ℃; for 1h; Molecular sieve;

With hydrogen sulfide; acetic acid; at 20 ℃; for 1h;
DOI:10.1021/ol200942g

Reference yield:

: C₂₁H₂₉NO₁₀

: 1309358-16-4
(2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanenitrile

Guidance literature:: Multi-step reaction with 8 steps

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

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

3.1: triethylamine / dichloromethane / 20 °C

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

5.1: 1H-imidazole / N,N-dimethyl-formamide / 3.16 h / 0 - 20 °C / Inert atmosphere

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C

7.1: ammonium hydroxide; water / 1,4-dioxane / 1 h / 20 °C

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C

8.2: 1 h / -78 - 20 °C / Molecular sieve

8.3: 1 h / 20 °C

With 1H-imidazole; ammonium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium 10% on activated carbon; tetrabutylammomium bromide; water; hydrogen; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
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

: 1309358-16-4
(2S,3R,4R,2'S,3'S)-2,3-(2',3'-dimethoxybutylene-2',3'-dioxy)-5-(tert-butyldiphenylsilyloxy)-4-[(tert-butyloxycarbonyl)aminomethyl]pentanenitrile

Guidance literature:: Multi-step reaction with 9 steps

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

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

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

4.1: triethylamine / dichloromethane / 20 °C

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

6.1: 1H-imidazole / N,N-dimethyl-formamide / 3.16 h / 0 - 20 °C / Inert atmosphere

7.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C

8.1: ammonium hydroxide; water / 1,4-dioxane / 1 h / 20 °C

9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C

9.2: 1 h / -78 - 20 °C / Molecular sieve

9.3: 1 h / 20 °C

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