N-(p-methoxybenzyl)-1,2-isopropylidene-D-glucofuranuronamide

Base Information

• Chemical Name: N-(p-methoxybenzyl)-1,2-isopropylidene-D-glucofuranuronamide
• CAS No.: 138610-59-0
• Molecular Formula: C₁₇H₂₃NO₇
• Molecular Weight: 353.372
• Mol file: 138610-59-0.mol

Synonyms:

Chemical Property of N-(p-methoxybenzyl)-1,2-isopropylidene-D-glucofuranuronamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(p-methoxybenzyl)-1,2-isopropylidene-D-glucofuranuronamide

There total 1 articles about N-(p-methoxybenzyl)-1,2-isopropylidene-D-glucofuranuronamide 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: 94.0%

4-methoxy-benzylamine (2393-23-9) + D-glucurono-3,6-lactone acetonide (3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1) → N-(p-methoxybenzyl)-1,2-isopropylidene-D-glucofuranuronamide (138610-59-0)

Guidance literature:

In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1246/cl.1991.2223

Reference yield: 85.0%

N-(p-methoxybenzyl)-1,2-isopropylidene-D-glucofuranuronamide (138610-59-0) → N-(p-methoxybenzyl)-D-glucopyranuronamide

Guidance literature:

With trifluoroacetic acid; Ambient temperature;

DOI:10.1246/cl.1991.2223

Reference yield:

N-(p-methoxybenzyl)-1,2-isopropylidene-D-glucofuranuronamide (138610-59-0) → (1S,4S,5R)-4-Hydroxy-6-(4-methoxy-benzyl)-8-oxa-6-aza-bicyclo[3.2.1]octan-7-one (138610-65-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / aq. CF₃COOH / Ambient temperature

2: 66 percent / pyridine / Ambient temperature

3: 38 percent / CF₃SO₃H / chlorobenzene / 0.5 h / 132 °C / other catalysts, solvents and temperatures

4: 100 percent / hydrogen / Pd/C / methanol / Ambient temperature

5: 96 percent / NaBH₄ / methanol / 30 °C

With pyridine; sodium tetrahydroborate; trifluorormethanesulfonic acid; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In methanol; chlorobenzene;

DOI:10.1246/cl.1991.2223

upstream raw materials:

4-methoxy-benzylamine

D-glucurono-3,6-lactone acetonide

Downstream raw materials:

(1S,4S,5R)-4-benzyloxy-8-oxa-6-azabicyclo<3.2.1>octan-7-one

(1S,4S,5R)-4-benzyloxy-8-oxa-6-azabicyclo<3.2.1>oct-2-en-7-one

(1S,4S,5R)-4-hydroxy-N-(p-methoxybenzyl)-8-oxa-6-azabicyclo<3.2.1>oct-2-ene-7-one

(1S,5R)-N-(p-methoxybenzyl)-8-oxa-6-azabicyclo<3.2.1>oct-2-ene-4,7-dione

Refernces