5-amino-1-(2',3'-O-isopropylidene-4'-hydroxymethylcyclopentyl)imidazole-4-dibenzyl glutamyl carboxamide

Base Information

Chemical Name:5-amino-1-(2',3'-O-isopropylidene-4'-hydroxymethylcyclopentyl)imidazole-4-dibenzyl glutamyl carboxamide
CAS No.:174088-47-2
Molecular Formula:C₃₂H₃₈N₄O₈
Molecular Weight:606.676
Hs Code.:

Synonyms:5-amino-1-(2',3'-O-isopropylidene-4'-hydroxymethylcyclopentyl)imidazole-4-dibenzyl glutamyl carboxamide

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Chemical Property of 5-amino-1-(2',3'-O-isopropylidene-4'-hydroxymethylcyclopentyl)imidazole-4-dibenzyl glutamyl carboxamide

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Technology Process of 5-amino-1-(2',3'-O-isopropylidene-4'-hydroxymethylcyclopentyl)imidazole-4-dibenzyl glutamyl carboxamide

There total 7 articles about 5-amino-1-(2',3'-O-isopropylidene-4'-hydroxymethylcyclopentyl)imidazole-4-dibenzyl glutamyl carboxamide 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: 50.0%

: 2768-50-5
dibenzyl L-glutamate

: 174088-46-1
5-Amino-1-((3aS,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-1H-imidazole-4-carboxylic acid

: 174088-47-2
5-amino-1-(2',3'-O-isopropylidene-4'-hydroxymethylcyclopentyl)imidazole-4-dibenzyl glutamyl carboxamide

Guidance literature:: With CF₃-HOBT; dicyclohexyl-carbodiimide; In acetonitrile; at 25 ℃; for 20h;
DOI:10.1080/15257779508010715

Reference yield:

: 135486-55-4
(1S,2S,3R,4S)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanol

: 174088-47-2
5-amino-1-(2',3'-O-isopropylidene-4'-hydroxymethylcyclopentyl)imidazole-4-dibenzyl glutamyl carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1: DMAP / pyridine / 2 h / 0 °C

2: NaN₃ / dimethylformamide / 1.) 0 deg C, 1 h, 2.) 25 deg C, 15 h

3: 97 percent / SnCl₂, thiophenol, Et₃N / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 25 deg C, 18 h

4: 96 percent / TBAF / tetrahydrofuran; H₂O / 1 h / 25 °C

5: 43 percent / acetonitrile / 19 h / 25 °C

6: H₂ / Pd/C / aq. ethanol / 4 h / 760 Torr

7: 50 percent / CF₃-HOBT, DCC / acetonitrile / 20 h / 25 °C

With dmap; sodium azide; CF₃-HOBT; tetrabutyl ammonium fluoride; hydrogen; thiophenol; triethylamine; dicyclohexyl-carbodiimide; tin(ll) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1080/15257779508010715

Reference yield:

: 135486-56-5
1-azido-2,3-O-isopropylidene-4-(tert-butyldimethylsilyloxymethyl)cyclopentane

: 174088-47-2
5-amino-1-(2',3'-O-isopropylidene-4'-hydroxymethylcyclopentyl)imidazole-4-dibenzyl glutamyl carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / SnCl₂, thiophenol, Et₃N / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 25 deg C, 18 h

2: 96 percent / TBAF / tetrahydrofuran; H₂O / 1 h / 25 °C

3: 43 percent / acetonitrile / 19 h / 25 °C

4: H₂ / Pd/C / aq. ethanol / 4 h / 760 Torr

5: 50 percent / CF₃-HOBT, DCC / acetonitrile / 20 h / 25 °C

With CF₃-HOBT; tetrabutyl ammonium fluoride; hydrogen; thiophenol; triethylamine; dicyclohexyl-carbodiimide; tin(ll) chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1080/15257779508010715