(3R,5R,6S)-5-[benzyl(hydroxy)amino]-3-bromo-6-(hydroxymethyl)-2,2-dimethyldihydro-2H-pyran-4(3H)-one

Base Information

• Chemical Name: (3R,5R,6S)-5-[benzyl(hydroxy)amino]-3-bromo-6-(hydroxymethyl)-2,2-dimethyldihydro-2H-pyran-4(3H)-one
• CAS No.: 1198077-59-6
• Molecular Formula: C₁₅H₂₀BrNO₄
• Molecular Weight: 358.232
• Mol file: 1198077-59-6.mol

Synonyms:(3R,5R,6S)-5-[benzyl(hydroxy)amino]-3-bromo-6-(hydroxymethyl)-2,2-dimethyldihydro-2H-pyran-4(3H)-one

Chemical Property of (3R,5R,6S)-5-[benzyl(hydroxy)amino]-3-bromo-6-(hydroxymethyl)-2,2-dimethyldihydro-2H-pyran-4(3H)-one

Chemical Property:

Purity/Quality:

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Technology Process of (3R,5R,6S)-5-[benzyl(hydroxy)amino]-3-bromo-6-(hydroxymethyl)-2,2-dimethyldihydro-2H-pyran-4(3H)-one

There total 1 articles about (3R,5R,6S)-5-[benzyl(hydroxy)amino]-3-bromo-6-(hydroxymethyl)-2,2-dimethyldihydro-2H-pyran-4(3H)-one 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: 70.0%

((2S,3R)-3-(benzyl(tert-butyldimethylsilyloxy)amino)-4-ethoxy-6,6-dimethyl-3,6-dihydro-2H-pyran-2-yl)methanol (1198077-53-0) → (3R,5R,6S)-5-[benzyl(hydroxy)amino]-3-bromo-6-(hydroxymethyl)-2,2-dimethyldihydro-2H-pyran-4(3H)-one (1198077-59-6)

Guidance literature:

With N-Bromosuccinimide; water; In acetonitrile; for 0.25h; Inert atmosphere;

DOI:10.1021/ol902354f

Reference yield: 87.0%

(3R,5R,6S)-5-[benzyl(hydroxy)amino]-3-bromo-6-(hydroxymethyl)-2,2-dimethyldihydro-2H-pyran-4(3H)-one (1198077-59-6) → (2S,3R,Z)-N-benzylidene-2-(hydroxymethyl)-6,6-dimethyl-4-oxotetrahydropyran-3-amine oxide (1198077-60-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol902354f DOI:10.3762/bjoc.6.75

upstream raw materials:

((2S,3R)-3-(benzyl(tert-butyldimethylsilyloxy)amino)-4-ethoxy-6,6-dimethyl-3,6-dihydro-2H-pyran-2-yl)methanol

Downstream raw materials:

(2S,3R,Z)-N-benzylidene-2-(hydroxymethyl)-6,6-dimethyl-4-oxotetrahydropyran-3-amine oxide