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

Base Information

• Chemical Name: ((2S,3R)-3-(benzyl(tert-butyldimethylsilyloxy)amino)-4-ethoxy-6,6-dimethyl-3,6-dihydro-2H-pyran-2-yl)methanol
• CAS No.: 1198077-53-0
• Molecular Formula: C₂₃H₃₉NO₄Si
• Molecular Weight: 421.652
• Mol file: 1198077-53-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about ((2S,3R)-3-(benzyl(tert-butyldimethylsilyloxy)amino)-4-ethoxy-6,6-dimethyl-3,6-dihydro-2H-pyran-2-yl)methanol 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: 84.0%

N-benzyl-O-(tert-butyldimethylsilyl)-N-((R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-ethoxyallyl)hydroxylamine (1198077-51-8) → ((2S,3R)-3-(benzyl(tert-butyldimethylsilyloxy)amino)-4-ethoxy-6,6-dimethyl-3,6-dihydro-2H-pyran-2-yl)methanol (1198077-53-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 - 20 ℃; for 6h; Inert atmosphere;

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

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: 52.0%

((2S,3R)-3-(benzyl(tert-butyldimethylsilyloxy)amino)-4-ethoxy-6,6-dimethyl-3,6-dihydro-2H-pyran-2-yl)methanol (1198077-53-0) → (3S,4R,5S,6S)-5-[benzyl(tert-butyldimethylsiloxy)amino]-6-(hydroxymethyl)-2,2-dimethyltetrahydro-2H-pyran-3,4-diol (1198077-63-2)

Guidance literature:

((2S,3R)-3-(benzyl(tert-butyldimethylsilyloxy)amino)-4-ethoxy-6,6-dimethyl-3,6-dihydro-2H-pyran-2-yl)methanol; With potassium osmate(VI) dihydrate; water; 4-methylmorpholine N-oxide; In acetone; at 20 ℃; for 72h; Inert atmosphere;

With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol902354f

upstream raw materials:

N-benzyl-O-(tert-butyldimethylsilyl)-N-((R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-ethoxyallyl)hydroxylamine

Downstream raw materials:

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

(3S,4R,5S,6S)-5-[benzyl(tert-butyldimethylsiloxy)amino]-6-(hydroxymethyl)-2,2-dimethyltetrahydro-2H-pyran-3,4-diol

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