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

Base Information

• Chemical Name: ⁽¹⁾-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide
• CAS No.: 1349097-36-4
• Molecular Formula: C₂₈H₄₃NO₄SSi
• Molecular Weight: 517.805

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

Chemical Property of ⁽¹⁾-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide

Chemical Property:

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Technology Process of ⁽¹⁾-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide

There total 4 articles about ⁽¹⁾-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-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:

2,3-Di-O-benzyl-4-O-(tert-butyldimethylsilyl)-D-erythrose (158535-88-7) + (R)-2-methylpropane-2-sulfinamide (196929-78-9) → (1)-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide (1349097-36-4)

Guidance literature:

With titanium(IV) tetraethanolate; In tetrahydrofuran; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ol202747p

Reference yield:

benzyl bromide (100-39-0) → (1)-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide (1349097-36-4)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; titanium(IV) tetraethanolate; calcium sulfate; trimethylaluminum; diisobutylaluminium hydride; silver(l) oxide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ol202747p

Reference yield:

(2R,3R)-2,3-bis(benzyloxy)-4-hydroxybutanoic acid 1,4-lactone (130412-79-2) → (1)-(RS,E,2S,3R)-N-[2,3-bis(benzyloxy)-4-(tert-butyldimethylsilyloxy)butylidene]-2-methylpropane-1-sulfinamide (1349097-36-4)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; titanium(IV) tetraethanolate; trimethylaluminum; diisobutylaluminium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol202747p

upstream raw materials:

benzyl bromide

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

(2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide

2,3-Di-O-benzyl-4-O-(tert-butyldimethylsilyl)-D-erythrose

Downstream raw materials:

(+)-(4S,5S)-4-{(1S,2R)-1,2-dibenzyloxy-3-[tert-butyldimethylsilyloxy]propyl}-5-ethynyloxazolidin-2-one

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

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

(-)-(RS,2S,3R,4R,5R)-N-[2,3-dibenzyloxy-1-hydroxy-5-(methoxymethoxy)hept-6-en-4-yl]-2-methylpropane-2-sulfinamide

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