methyl 5-azido-N-benzyloxycarbonyl-2,5,6-trideoxy-2,6-imino-3-O-(4-methoxybenzyl)-α-L-gulofuranoside

Base Information

Chemical Name:methyl 5-azido-N-benzyloxycarbonyl-2,5,6-trideoxy-2,6-imino-3-O-(4-methoxybenzyl)-α-L-gulofuranoside
CAS No.:152456-31-0
Molecular Formula:C₂₃H₂₆N₄O₆
Molecular Weight:454.483
Hs Code.:

Synonyms:methyl 5-azido-N-benzyloxycarbonyl-2,5,6-trideoxy-2,6-imino-3-O-(4-methoxybenzyl)-α-L-gulofuranoside

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Chemical Property of methyl 5-azido-N-benzyloxycarbonyl-2,5,6-trideoxy-2,6-imino-3-O-(4-methoxybenzyl)-α-L-gulofuranoside

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Technology Process of methyl 5-azido-N-benzyloxycarbonyl-2,5,6-trideoxy-2,6-imino-3-O-(4-methoxybenzyl)-α-L-gulofuranoside

There total 6 articles about methyl 5-azido-N-benzyloxycarbonyl-2,5,6-trideoxy-2,6-imino-3-O-(4-methoxybenzyl)-α-L-gulofuranoside 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%

: (1S,4R,5S,7S,8R)-7-Methoxy-8-(4-methoxy-benzyloxy)-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester

: (1S,4R,5R,7S,8R)-4-Azido-7-methoxy-8-(4-methoxy-benzyloxy)-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester

: 152456-31-0
methyl 5-azido-N-benzyloxycarbonyl-2,5,6-trideoxy-2,6-imino-3-O-(4-methoxybenzyl)-α-L-gulofuranoside

Guidance literature:: With sodium azide; tetra(n-butyl)ammonium hydrogensulfate; In N,N-dimethyl-formamide; at 60 ℃; for 18h;

Reference yield:

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

: 152456-31-0
methyl 5-azido-N-benzyloxycarbonyl-2,5,6-trideoxy-2,6-imino-3-O-(4-methoxybenzyl)-α-L-gulofuranoside

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

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

: 152456-31-0
methyl 5-azido-N-benzyloxycarbonyl-2,5,6-trideoxy-2,6-imino-3-O-(4-methoxybenzyl)-α-L-gulofuranoside

Guidance literature:: Multi-step reaction with 4 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

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