(4S,5S)-1,3-Dibenzyl-5-((R)-1-benzyloxy-2,3-dihydroxy-propyl)-2-oxo-imidazolidine-4-carboxylic acid methyl ester

Base Information

Chemical Name:(4S,5S)-1,3-Dibenzyl-5-((R)-1-benzyloxy-2,3-dihydroxy-propyl)-2-oxo-imidazolidine-4-carboxylic acid methyl ester
CAS No.:780767-59-1
Molecular Formula:C₂₉H₃₂N₂O₆
Molecular Weight:504.583
Hs Code.:

Synonyms:(4S,5S)-1,3-Dibenzyl-5-((R)-1-benzyloxy-2,3-dihydroxy-propyl)-2-oxo-imidazolidine-4-carboxylic acid methyl ester

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Chemical Property of (4S,5S)-1,3-Dibenzyl-5-((R)-1-benzyloxy-2,3-dihydroxy-propyl)-2-oxo-imidazolidine-4-carboxylic acid methyl ester

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Technology Process of (4S,5S)-1,3-Dibenzyl-5-((R)-1-benzyloxy-2,3-dihydroxy-propyl)-2-oxo-imidazolidine-4-carboxylic acid methyl ester

There total 10 articles about (4S,5S)-1,3-Dibenzyl-5-((R)-1-benzyloxy-2,3-dihydroxy-propyl)-2-oxo-imidazolidine-4-carboxylic acid methyl ester 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%

: 67-56-1
methanol

: 780767-58-0
Acetic acid (R)-3-benzyloxy-3-((4S,5S)-1,3-dibenzyl-5-cyano-2-oxo-imidazolidin-4-yl)-2-oxo-propyl ester

: 780767-59-1
(4S,5S)-1,3-Dibenzyl-5-((R)-1-benzyloxy-2,3-dihydroxy-propyl)-2-oxo-imidazolidine-4-carboxylic acid methyl ester

Guidance literature:: Acetic acid (R)-3-benzyloxy-3-((4S,5S)-1,3-dibenzyl-5-cyano-2-oxo-imidazolidin-4-yl)-2-oxo-propyl ester; With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 4h;

methanol; With chloro-trimethyl-silane; at 40 ℃; for 4h; Further stages.;
DOI:10.1016/j.tetlet.2004.08.019

Reference yield:

: 14131-63-6
D-glucosamine hydrochloride

: 780767-59-1
(4S,5S)-1,3-Dibenzyl-5-((R)-1-benzyloxy-2,3-dihydroxy-propyl)-2-oxo-imidazolidine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: aq. NaHCO₃ / dioxane / 20 °C

2.1: pyridine / H₂O / 55 °C

3.1: p-TSA / 20 °C

4.1: NaH / dimethylformamide / 6 h / 0 - 20 °C

5.1: 98 percent / p-TSA / tetrahydrofuran; H₂O / 6 h / Heating

6.1: NaIO₄ / acetone; H₂O / 0.5 h / 20 °C

7.1: Et₃N; DMAP / 1,2-dichloro-ethane / 4 h / Heating

8.1: 62 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -78 - 20 °C

9.1: NaBH₄ / methanol / 4 h / 0 - 20 °C

9.2: 93 percent / TMSCl / 4 h / 40 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; boron trifluoride diethyl etherate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tetlet.2004.08.019

Reference yield:

: 100-39-0
benzyl bromide

: 780767-59-1
(4S,5S)-1,3-Dibenzyl-5-((R)-1-benzyloxy-2,3-dihydroxy-propyl)-2-oxo-imidazolidine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 6 h / 0 - 20 °C

2.1: 98 percent / p-TSA / tetrahydrofuran; H₂O / 6 h / Heating

3.1: NaIO₄ / acetone; H₂O / 0.5 h / 20 °C

4.1: Et₃N; DMAP / 1,2-dichloro-ethane / 4 h / Heating

5.1: 62 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -78 - 20 °C

6.1: NaBH₄ / methanol / 4 h / 0 - 20 °C

6.2: 93 percent / TMSCl / 4 h / 40 °C

With dmap; sodium tetrahydroborate; sodium periodate; boron trifluoride diethyl etherate; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tetlet.2004.08.019