2-azido-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol

Base Information

Chemical Name:2-azido-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol
CAS No.:152456-34-3
Molecular Formula:C₃₇H₄₈N₄O₈Si
Molecular Weight:704.896
Hs Code.:

2-azido-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol

Synonyms:2-azido-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol

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Chemical Property of 2-azido-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol

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Technology Process of 2-azido-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol

There total 10 articles about 2-azido-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol 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%

: 77902-89-7
benzyl <(trifluoromethyl)sulfonyloxy>acetate

: 152456-33-2
2-azido-N-benzyloxycarbonyl-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol

: 152456-34-3
2-azido-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -55 ℃; for 0.5h;

Reference yield:

: methyl 6-azido-5-O-benzyl-6-deoxy-3-O-(4-methoxybenzyl)-2-O-(trifluoromethylsulfonyl)-D-glucofuranoside

: 152456-34-3
2-azido-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol

Guidance literature:: Multi-step reaction with 8 steps

1: 2.0 g / sodium acetate, ammonium formate / 10percent Pd on carbon / methanol / 20 h / Ambient temperature

2: 1.10 g / aq. sodium hydrogen carbonate / dioxane / 3 h / Ambient temperature

3: 74 percent / CG 120 (H⁺) ion-exchange resin / methanol / 0.5 h / Heating

4: CH₂Cl₂; pyridine / 1 h / -30 °C

5: 58 percent / NaN₃, tetrabutylammonium hydrogen sulfate / dimethylformamide / 18 h / 60 °C

6: 1.) HCl, 2.) sodium borohydride / 1.) THF, room temperature, 15 min, 2.) EtOH, water, 0 deg C, 15 min

7: 82 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 24 h / Ambient temperature

8: 50 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / -55 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; sodium azide; CG 120 (H⁺) ion-exchange resin; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; ammonium formate; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 152456-34-3
2-azido-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6-O-(tert-butyldimethylsilyl)-1,2,5-trideoxy-1,5-imino-4-O-(4-methoxybenzyl)-D-glucitol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.10 g / aq. sodium hydrogen carbonate / dioxane / 3 h / Ambient temperature

2: 74 percent / CG 120 (H⁺) ion-exchange resin / methanol / 0.5 h / Heating

3: CH₂Cl₂; pyridine / 1 h / -30 °C

4: 58 percent / NaN₃, tetrabutylammonium hydrogen sulfate / dimethylformamide / 18 h / 60 °C

5: 1.) HCl, 2.) sodium borohydride / 1.) THF, room temperature, 15 min, 2.) EtOH, water, 0 deg C, 15 min

6: 82 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 24 h / Ambient temperature

7: 50 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / -55 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; sodium azide; CG 120 (H⁺) ion-exchange resin; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;