(S(S))-N-((3S,4R,5S)-5-benzyloxy-3-(methoxymethoxy)-1-trimethylsilylhex-1-yn-4-yl)-2-methylpropane-2-sulfinamide

Base Information

• Chemical Name: (S(S))-N-((3S,4R,5S)-5-benzyloxy-3-(methoxymethoxy)-1-trimethylsilylhex-1-yn-4-yl)-2-methylpropane-2-sulfinamide
• CAS No.: 1114435-46-9
• Molecular Formula: C₂₂H₃₇NO₄SSi
• Molecular Weight: 439.692

Synonyms:(S(S))-N-((3S,4R,5S)-5-benzyloxy-3-(methoxymethoxy)-1-trimethylsilylhex-1-yn-4-yl)-2-methylpropane-2-sulfinamide

Chemical Property of (S(S))-N-((3S,4R,5S)-5-benzyloxy-3-(methoxymethoxy)-1-trimethylsilylhex-1-yn-4-yl)-2-methylpropane-2-sulfinamide

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Technology Process of (S(S))-N-((3S,4R,5S)-5-benzyloxy-3-(methoxymethoxy)-1-trimethylsilylhex-1-yn-4-yl)-2-methylpropane-2-sulfinamide

There total 2 articles about (S(S))-N-((3S,4R,5S)-5-benzyloxy-3-(methoxymethoxy)-1-trimethylsilylhex-1-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: 76.0%

(S)-N-((S)-2-(benzyloxy)propylidene)-2-methylpropane-2-sulfinamide + (methoxymethyl)[(3-trimethylsilyl)prop-2-ynyl]ether (33322-70-2) → (S(S))-N-((3S,4R,5S)-5-benzyloxy-3-(methoxymethoxy)-1-trimethylsilylhex-1-yn-4-yl)-2-methylpropane-2-sulfinamide (1114435-46-9)

Guidance literature:

(methoxymethyl)[(3-trimethylsilyl)prop-2-ynyl]ether; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; hexane; cyclohexane; at -78 ℃; for 1h; Inert atmosphere;

With zinc dibromide; In diethyl ether; hexane; cyclohexane; at -78 ℃; for 0.333333h; Inert atmosphere;

(S)-N-((S)-2-(benzyloxy)propylidene)-2-methylpropane-2-sulfinamide; optical yield given as %de; stereoselective reaction; Further stages;

DOI:10.1021/ol802912f

Reference yield: 76.0%

3-methoxymethoxy-1-(trimethylsilyl)allenylzinc bromide + (S)-N-((S)-2-(benzyloxy)propylidene)-2-methylpropane-2-sulfinamide → (S(S))-N-((3S,4R,5S)-5-benzyloxy-3-(methoxymethoxy)-1-trimethylsilylhex-1-yn-4-yl)-2-methylpropane-2-sulfinamide (1114435-46-9)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; In diethyl ether; at -80 ℃; for 2h; diastereoselective reaction;

DOI:10.1016/j.tetasy.2010.04.044

Reference yield: 59.0%

(S(S))-N-((3S,4R,5S)-5-benzyloxy-3-(methoxymethoxy)-1-trimethylsilylhex-1-yn-4-yl)-2-methylpropane-2-sulfinamide (1114435-46-9) → C16H25NO2Si (1149335-73-8)

Guidance literature:

With hydrogenchloride; methanol; In 1,4-dioxane; for 2.5h; Inert atmosphere; Reflux;

DOI:10.1021/ol802912f

upstream raw materials:

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

Downstream raw materials:

C₁₆H₂₅NO₂Si

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