N-[(2R,3S,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide

Base Information

Chemical Name:N-[(2R,3S,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide
CAS No.:131070-35-4
Molecular Formula:C₂₂H₃₃NO₁₁
Molecular Weight:487.504
Hs Code.:

N-[(2R,3S,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide

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Chemical Property of N-[(2R,3S,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide

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Technology Process of N-[(2R,3S,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide

There total 8 articles about N-[(2R,3S,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide 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: 83.0%

: 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

: 131070-35-4,131070-36-5
N-[(2R,3S,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: With acetyl chloride; In methanol; for 23h;
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

: 131070-35-4,131070-36-5
N-[(2R,3S,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide

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: 83 percent / acetyl chloride / methanol / 23 h

With 1H-imidazole; lithium aluminium tetrahydride; hydroxylamine hydrochloride; tetrabutylammomium bromide; potassium acetate; sodium acetate; sodium hydride; acetyl chloride; 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

: 131070-35-4,131070-36-5
N-[(2R,3S,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R,5R)-4,5-dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-acetamide

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: 83 percent / acetyl chloride / methanol / 23 h

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