(R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

Base Information

Chemical Name:(R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one
CAS No.:929882-93-9
Molecular Formula:C₄₇H₈₁NO₈Si₃
Molecular Weight:872.419
Hs Code.:

Synonyms:(R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

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Chemical Property of (R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

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Technology Process of (R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

There total 2 articles about (R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-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: 94.0%

: 929882-83-7
(R)-3-((2R,3S,4S,5R,7R,9S)-10-(benzyloxy)-7,9-bis(tert-butyldimethylsilyloxy)-3,5-dihydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 929882-93-9
(R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -5 ℃; for 1h;
DOI:10.1002/anie.200603654

Reference yield:

: 929882-82-6
(2R,4S,5R,7R,9S)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-10-(benzyloxy)-7,9-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4-dimethyldecane-1,3-dione

: 929882-93-9
(R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 77 percent / tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 15 h / -20 - 0 °C

2: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -5 °C

With 2,6-dimethylpyridine; acetic acid; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetonitrile;
DOI:10.1002/anie.200603654

Reference yield:

: 929882-93-9
(R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

: 929883-07-8
(2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: lithium borohydride / diethyl ether; H₂O / 1 h / 0 °C

2: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h / 20 °C

3: 91 percent / BH₃*THF; Sc(OTf)3 / CH₂Cl₂; tetrahydrofuran / 1 h

4: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h

5: 88 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 1.83 h / 20 °C / atmospheric pressure

With 2,6-dimethylpyridine; lithium borohydride; borane-THF; hydrogen; pyridinium p-toluenesulfonate; scandium tris(trifluoromethanesulfonate); palladium dihydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1002/anie.200603654