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

Base Information

Chemical Name:(4S,5S)-5-benzyloxymethyl-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-1,3-oxazolidine
CAS No.:918299-94-2
Molecular Formula:C₃₅H₄₇NO₅Si
Molecular Weight:589.847
Hs Code.:

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

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

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

There total 8 articles about (4S,5S)-5-benzyloxymethyl-3-N-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-2,2-dimethyl-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: 93.0%

: 918299-93-1
(4S,5S)-5-benzyloxymethyl-3-N-tert-butoxycarbonyl-2,2-dimethyl-4-hydroxymethyl-1,3-oxazolidine

: 58479-61-1
tert-butylchlorodiphenylsilane

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

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1016/j.tet.2006.08.049

Reference yield:

: 148407-37-8
(2R,3R)-4-benzyloxy-2,3-epoxybutanoic acid methyl ester

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

Guidance literature:: Multi-step reaction with 7 steps

1: 300 mg / NaBr; Amberlyst 15 / acetone / 6 h / -20 °C

2: 265 mg / NaN₃ / dimethylformamide / 24 h / 20 °C

3: 335 mg / H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C

4: 348 mg / p-TsOH / CH₂Cl₂ / 3 h / 20 °C

5: 97 percent / DIBAL / toluene / 2 h / cooling

6: 96 percent / NaBH₄ / propan-2-ol; tetrahydrofuran / 2 h / cooling

7: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

With dmap; sodium tetrahydroborate; sodium azide; Amberlyst 15; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; sodium bromide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene;
DOI:10.1016/j.tet.2006.08.049

Reference yield:

: 918299-88-4
(2S,3R)-4-benzyloxy-2-bromo-3-hydroxybutanoic acid methyl ester

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

Guidance literature:: Multi-step reaction with 6 steps

1: 265 mg / NaN₃ / dimethylformamide / 24 h / 20 °C

2: 335 mg / H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C

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

4: 97 percent / DIBAL / toluene / 2 h / cooling

5: 96 percent / NaBH₄ / propan-2-ol; tetrahydrofuran / 2 h / cooling

6: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

With dmap; sodium tetrahydroborate; sodium azide; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1016/j.tet.2006.08.049