1-allyl-6(S)-benzyl-5(R)-t-butyldimethylsilyloxy-4(S)-hydroxymethyl-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine

Base Information

Chemical Name:1-allyl-6(S)-benzyl-5(R)-t-butyldimethylsilyloxy-4(S)-hydroxymethyl-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine
CAS No.:256419-16-6
Molecular Formula:C₂₉H₄₂N₂O₄Si
Molecular Weight:510.749
Hs Code.:

Synonyms:1-allyl-6(S)-benzyl-5(R)-t-butyldimethylsilyloxy-4(S)-hydroxymethyl-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine

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Chemical Property of 1-allyl-6(S)-benzyl-5(R)-t-butyldimethylsilyloxy-4(S)-hydroxymethyl-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine

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Technology Process of 1-allyl-6(S)-benzyl-5(R)-t-butyldimethylsilyloxy-4(S)-hydroxymethyl-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine

There total 6 articles about 1-allyl-6(S)-benzyl-5(R)-t-butyldimethylsilyloxy-4(S)-hydroxymethyl-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine 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: 58.0%

: 256419-14-4
1-allyl-6(S)-benzyl-5(R)-t-butyl-dimethylsilyloxy-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine-4(R)-carboxylic acid ethyl ester

: 256419-16-6
1-allyl-6(S)-benzyl-5(R)-t-butyldimethylsilyloxy-4(S)-hydroxymethyl-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine

Guidance literature:: With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; ethanol; at 20 ℃; for 96h;
DOI:10.1007/PL00010189

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 256419-16-6
1-allyl-6(S)-benzyl-5(R)-t-butyldimethylsilyloxy-4(S)-hydroxymethyl-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole / CH₂Cl₂ / 20 h / 20 °C

2: imidazole / CH₂Cl₂ / 1 h / 20 °C / pH 7 - 8

3: 61 percent / NaH / dimethylformamide / 0.67 h / 20 °C

4: 58 percent / NaBH₄; LiCl / ethanol; tetrahydrofuran / 96 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; sodium hydride; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: cyclocondensation / 3: Alkylation / 4: Reduction;
DOI:10.1007/PL00010189

Reference yield:

: 164515-05-3
(2R,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2-<(4-methoxybenzyl)amino>-5-phenylpentanoic acid ethyl ester

: 256419-16-6
1-allyl-6(S)-benzyl-5(R)-t-butyldimethylsilyloxy-4(S)-hydroxymethyl-3-(4-methoxybenzyl)-2-oxo-hexahydropyrimidine

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / aq. HCl / CH₂Cl₂ / 1 h / 20 °C

2: imidazole / CH₂Cl₂ / 20 h / 20 °C

3: imidazole / CH₂Cl₂ / 1 h / 20 °C / pH 7 - 8

4: 61 percent / NaH / dimethylformamide / 0.67 h / 20 °C

5: 58 percent / NaBH₄; LiCl / ethanol; tetrahydrofuran / 96 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium hydride; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Hydrolysis / 2: silylation / 3: cyclocondensation / 4: Alkylation / 5: Reduction;
DOI:10.1007/PL00010189