(+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

Base Information

Chemical Name:(+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide
CAS No.:1349097-42-2
Molecular Formula:C₃₆H₅₉NO₆SSi₂
Molecular Weight:690.105
Hs Code.:

(+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

Synonyms:(+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

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Chemical Property of (+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

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Technology Process of (+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

There total 5 articles about (+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide 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: 75.0%

: 1349097-36-4
⁽¹⁾-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide

: 33322-70-2
(methoxymethyl)[(3-trimethylsilyl)prop-2-ynyl]ether

: 1349097-40-0
(-)-(RS,2S,3R,4R,5R)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

: 1349097-42-2
(+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

Guidance literature:: (methoxymethyl)[(3-trimethylsilyl)prop-2-ynyl]ether; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; hexane; cyclohexane; at -80 ℃; for 1h; Inert atmosphere;

With zinc dibromide; In diethyl ether; hexane; cyclohexane; at -80 ℃; for 0.333333h; Inert atmosphere;

⁽¹⁾-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide; In diethyl ether; hexane; cyclohexane; at -80 ℃; for 1h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol202747p

Reference yield:

: 100-39-0
benzyl bromide

: 1349097-42-2
(+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: calcium sulfate; silver(l) oxide / acetonitrile / 48 h / 20 °C / Darkness

2.1: trimethylaluminum / tetrahydrofuran; toluene / 0.5 h / 0 - 20 °C

2.2: 17 h / -15 - 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 °C

4.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -80 - -78 °C / Inert atmosphere

5.1: titanium(IV) tetraethanolate / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

6.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; hexane; cyclohexane / 1 h / -80 °C / Inert atmosphere

6.2: 0.33 h / -80 °C / Inert atmosphere

6.3: 1 h / -80 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) tetraethanolate; calcium sulfate; N,N,N,N,-tetramethylethylenediamine; trimethylaluminum; sec.-butyllithium; diisobutylaluminium hydride; silver(l) oxide; In tetrahydrofuran; diethyl ether; hexane; cyclohexane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ol202747p

Reference yield:

: 130412-79-2
(2R,3R)-2,3-bis(benzyloxy)-4-hydroxybutanoic acid 1,4-lactone

: 1349097-42-2
(+)-(RS,2S,3R,4S,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: trimethylaluminum / tetrahydrofuran; toluene / 0.5 h / 0 - 20 °C

1.2: 17 h / -15 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 °C

3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -80 - -78 °C / Inert atmosphere

4.1: titanium(IV) tetraethanolate / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; hexane; cyclohexane / 1 h / -80 °C / Inert atmosphere

5.2: 0.33 h / -80 °C / Inert atmosphere

5.3: 1 h / -80 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) tetraethanolate; N,N,N,N,-tetramethylethylenediamine; trimethylaluminum; sec.-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; cyclohexane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol202747p