4-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Base Information

Chemical Name:4-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
CAS No.:131070-19-4
Molecular Formula:C₂₉H₄₅NO₁₂
Molecular Weight:599.676
Hs Code.:

Synonyms:4-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

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Chemical Property of 4-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

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Technology Process of 4-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

There total 9 articles about 4-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 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: 73.0%

: 131070-18-3
4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

: 131070-20-7
N-{(2R,3S,4R,5S,6R)-4-Benzyloxy-2-[(1R,2R)-1-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-propoxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

: 131070-19-4
4-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; for 8h;
DOI:10.1016/0008-6215(90)80149-W

Reference yield:

: 72200-55-6
2,3:5,6-Di-O-isopropylidene-4-O-(4',6'-O-isopropylidene-α-D-glucopyranosyl)-aldehydo-D-glucose dimethyl acetal

: 131070-19-4
4-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / imidazole / dimethylformamide / 5 h / 0 deg C --> room temperature

2: 68 percent / pyridinium chlorochromate, potassium acetate / benzene / 2 h / Heating

3: 97 percent / hydroxylamine hydrochloride, sodium acetate / methanol; H₂O; acetic acid / 4 h

4: lithium aluminium hydride / tetrahydrofuran

5: 86 percent / methanol / 2 h

6: 1.) sodium hydride, 2.) tetrabutylammonium bromide / 1.) tetrahydrofuran, 0 deg C, 10 min, 2.) 12 h

7: 73 percent / pyridinium p-toluenesulfonate / methanol / 8 h

With 1H-imidazole; lithium aluminium tetrahydride; hydroxylamine hydrochloride; tetrabutylammomium bromide; potassium acetate; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; methanol; water; acetic acid; N,N-dimethyl-formamide; benzene;
DOI:10.1016/0008-6215(90)80149-W

Reference yield:

: 131070-11-6
4-O-(3-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

: 131070-19-4
4-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Guidance literature:: Multi-step reaction with 6 steps

1: 68 percent / pyridinium chlorochromate, potassium acetate / benzene / 2 h / Heating

2: 97 percent / hydroxylamine hydrochloride, sodium acetate / methanol; H₂O; acetic acid / 4 h

3: lithium aluminium hydride / tetrahydrofuran

4: 86 percent / methanol / 2 h

5: 1.) sodium hydride, 2.) tetrabutylammonium bromide / 1.) tetrahydrofuran, 0 deg C, 10 min, 2.) 12 h

6: 73 percent / pyridinium p-toluenesulfonate / methanol / 8 h

With lithium aluminium tetrahydride; hydroxylamine hydrochloride; tetrabutylammomium bromide; potassium acetate; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; methanol; water; acetic acid; benzene;
DOI:10.1016/0008-6215(90)80149-W