(4S,5S)-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-5-hydroxymethyl-1,3-oxazolidine

Base Information

Chemical Name:(4S,5S)-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-5-hydroxymethyl-1,3-oxazolidine
CAS No.:918299-95-3
Molecular Formula:C₂₈H₄₁NO₅Si
Molecular Weight:499.723
Hs Code.:

Synonyms:(4S,5S)-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-5-hydroxymethyl-1,3-oxazolidine

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Chemical Property of (4S,5S)-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-5-hydroxymethyl-1,3-oxazolidine

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Technology Process of (4S,5S)-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-5-hydroxymethyl-1,3-oxazolidine

There total 5 articles about (4S,5S)-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-5-hydroxymethyl-1,3-oxazolidine 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: 95.0%

: 918299-94-2
(4S,5S)-5-benzyloxymethyl-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-1,3-oxazolidine

: 918299-95-3
(4S,5S)-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-5-hydroxymethyl-1,3-oxazolidine

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 3h;
DOI:10.1016/j.tet.2006.08.049

Reference yield:

: 918299-92-0
(4R,5S)-5-benzyloxymethyl-3-N-tert-butoxycarbonyl-4-formyl-2,2-dimethyl-1,3-oxazolidine

: 918299-95-3
(4S,5S)-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-5-hydroxymethyl-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / NaBH₄ / propan-2-ol; tetrahydrofuran / 2 h / cooling

2: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

3: 95 percent / H₂ / Pd/C / methanol / 3 h / 20 °C

With dmap; sodium tetrahydroborate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol;
DOI:10.1016/j.tet.2006.08.049

Reference yield:

: 918299-90-8
(2R,3S)-4-benzyloxy-2-tert-butoxycarbonylamino-3-hydroxybutanoic acid methyl ester

: 918299-95-3
(4S,5S)-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-5-hydroxymethyl-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 5 steps

1: 348 mg / p-TsOH / CH₂Cl₂ / 3 h / 20 °C

2: 97 percent / DIBAL / toluene / 2 h / cooling

3: 96 percent / NaBH₄ / propan-2-ol; tetrahydrofuran / 2 h / cooling

4: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

5: 95 percent / H₂ / Pd/C / methanol / 3 h / 20 °C

With dmap; sodium tetrahydroborate; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; isopropyl alcohol; toluene;
DOI:10.1016/j.tet.2006.08.049