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

Base Information

Chemical Name:(+)-(RS,2S,3R,4R,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-(methoxymethoxy)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide
CAS No.:1349097-57-9
Molecular Formula:C₃₃H₅₁NO₆SSi
Molecular Weight:617.923
Hs Code.:

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

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

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

There total 7 articles about (+)-(RS,2S,3R,4R,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-(methoxymethoxy)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:

: 1349097-46-6
(-)-(RS,2S,3R,4R,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-methoxymethoxy-7-(trimethylsilyl)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

: 1349097-57-9
(+)-(RS,2S,3R,4R,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-(methoxymethoxy)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

Guidance literature:: With potassium carbonate; In methanol; at 0 ℃; for 2h;
DOI:10.1021/ol202747p

Reference yield:

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

: 1349097-57-9
(+)-(RS,2S,3R,4R,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-(methoxymethoxy)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -95 °C / Inert atmosphere

1.2: 0.08 h / -95 - -80 °C / Inert atmosphere

1.3: 1 h / -80 °C / Inert atmosphere

2.1: potassium carbonate / methanol / 2 h / 0 °C

With tert.-butyl lithium; potassium carbonate; In tetrahydrofuran; methanol; pentane;
DOI:10.1021/ol202747p

Reference yield:

: 100-39-0
benzyl bromide

: 1349097-57-9
(+)-(RS,2S,3R,4R,5S)-N-[1-(tert-butyldimethylsilyloxy)-2,3-dibenzyloxy-5-(methoxymethoxy)hept-6-yn-4-yl]-2-methylpropane-2-sulfinamide

Guidance literature:: Multi-step reaction with 7 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: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -95 °C / Inert atmosphere

6.2: 0.08 h / -95 - -80 °C / Inert atmosphere

6.3: 1 h / -80 °C / Inert atmosphere

7.1: potassium carbonate / methanol / 2 h / 0 °C

With 1H-imidazole; titanium(IV) tetraethanolate; calcium sulfate; trimethylaluminum; tert.-butyl lithium; diisobutylaluminium hydride; potassium carbonate; silver(l) oxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; acetonitrile; pentane;
DOI:10.1021/ol202747p