N-[(3R,5S)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-2-methylnon-6-yn-3-yl]-4-methylphenylsulfonamide

Base Information

• Chemical Name: N-[(3R,5S)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-2-methylnon-6-yn-3-yl]-4-methylphenylsulfonamide
• CAS No.: 1244779-52-9
• Molecular Formula: C₂₃H₃₉NO₄SSi
• Molecular Weight: 453.718

Synonyms:N-[(3R,5S)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-2-methylnon-6-yn-3-yl]-4-methylphenylsulfonamide

Chemical Property of N-[(3R,5S)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-2-methylnon-6-yn-3-yl]-4-methylphenylsulfonamide

Chemical Property:

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Technology Process of N-[(3R,5S)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-2-methylnon-6-yn-3-yl]-4-methylphenylsulfonamide

There total 1 articles about N-[(3R,5S)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-2-methylnon-6-yn-3-yl]-4-methylphenylsulfonamide 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:

(S)-4-methyl-3-tosylamino-1-pentanal (1161012-82-3) + 4-(tert-butyldimethylsilyloxy)-1-butyne (78592-82-2) → N-[(3R,5S)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-2-methylnon-6-yn-3-yl]-4-methylphenylsulfonamide (1244779-52-9) + N-[(3R,5R)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-2-methylnon-6-yn-3-yl]-4-methylphenylsulfonamide (1244779-51-8)

Guidance literature:

4-(tert-butyldimethylsilyloxy)-1-butyne; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

(S)-4-methyl-3-tosylamino-1-pentanal; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

DOI:10.1002/chem.201000653

Reference yield: 83.0%

N-[(3R,5S)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-2-methylnon-6-yn-3-yl]-4-methylphenylsulfonamide (1244779-52-9) → (2R,4R)-[4-(tet-butyldimethylsilyloxy)but-1-yn-2-yl]-4-isopropyl-N-(4-methylphenylsulfonyl)azetidine

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.333333h;

DOI:10.1002/chem.201000653

Reference yield: 32.0%

N-[(3R,5S)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-2-methylnon-6-yn-3-yl]-4-methylphenylsulfonamide (1244779-52-9) + 1,1'-carbonyldiimidazole (530-62-1) → (4R,6S)-6-[4-(tert-butyldimetylsilyloxy)but-1-yn-1-yl]-4-isopropyl-3-(4-methylsulfonyl)-1,3-oxazinan-2-one (1244779-60-9)

Guidance literature:

In N,N-dimethyl-formamide; at 90 ℃; for 248h;

DOI:10.1002/chem.201000653

upstream raw materials:

(S)-4-methyl-3-tosylamino-1-pentanal

4-(tert-butyldimethylsilyloxy)-1-butyne

Downstream raw materials:

(4R,6S)-6-[4-(tert-butyldimetylsilyloxy)but-1-yn-1-yl]-4-isopropyl-3-(4-methylsulfonyl)-1,3-oxazinan-2-one

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