1,2,4-tri-O-acetyl-3-amino-N-benzyloxycarbonyl-3,6-dideoxy-β-L-glucopyranose

Base Information

Chemical Name:1,2,4-tri-O-acetyl-3-amino-N-benzyloxycarbonyl-3,6-dideoxy-β-L-glucopyranose
CAS No.:1392477-15-4
Molecular Formula:C₂₀H₂₅NO₉
Molecular Weight:423.42
Hs Code.:

Synonyms:

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Chemical Property of 1,2,4-tri-O-acetyl-3-amino-N-benzyloxycarbonyl-3,6-dideoxy-β-L-glucopyranose

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Technology Process of 1,2,4-tri-O-acetyl-3-amino-N-benzyloxycarbonyl-3,6-dideoxy-β-L-glucopyranose

There total 9 articles about 1,2,4-tri-O-acetyl-3-amino-N-benzyloxycarbonyl-3,6-dideoxy-β-L-glucopyranose 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:

: 1189128-39-9
(2S,4R,5S,6E)-4-bromo-2-(tert-butyldimethylsilyloxy)-5-hydroxy-6-octen-3-one

: 1392477-15-4
1,2,4-tri-O-acetyl-3-amino-N-benzyloxycarbonyl-3,6-dideoxy-β-L-glucopyranose

Guidance literature:: Multi-step reaction with 9 steps

1: sodium azide / dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere

2: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / -35 - -20 °C / Inert atmosphere

3: pyridinium p-toluenesulfonate / dichloromethane / 20 °C / Inert atmosphere

4: water; trimethylphosphane / tetrahydrofuran / 36 h / 20 °C / Inert atmosphere

5: sodium hydrogencarbonate / methanol / 1.58 h / 0 - 20 °C / Inert atmosphere

6: 2,6-dimethylpyridine; sodium periodate; potassium osmate(VI) dihydrate / 1,4-dioxane; water / 2 h / 20 °C

7: sodium carbonate / methanol / 36 h / 20 °C / Inert atmosphere

8: hydrogen fluoride / acetonitrile / 6 h / 20 °C / Inert atmosphere

9: pyridine / 24 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; potassium osmate(VI) dihydrate; sodium periodate; sodium azide; hydrogen fluoride; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; sodium carbonate; acetic acid; tetramethylammonium triacetoxyborohydride; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile; 4: Staudinger reaction;
DOI:10.1039/c2ob25793a

Reference yield:

: 1392476-99-1
(2S,3R,4S,5S,6E)-4-azido-2-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-6-octene-2,3,5-triol

: 1392477-15-4
1,2,4-tri-O-acetyl-3-amino-N-benzyloxycarbonyl-3,6-dideoxy-β-L-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: water; trimethylphosphane / tetrahydrofuran / 36 h / 20 °C / Inert atmosphere

2: sodium hydrogencarbonate / methanol / 1.58 h / 0 - 20 °C / Inert atmosphere

3: 2,6-dimethylpyridine; sodium periodate; potassium osmate(VI) dihydrate / 1,4-dioxane; water / 2 h / 20 °C

4: sodium carbonate / methanol / 36 h / 20 °C / Inert atmosphere

5: hydrogen fluoride / acetonitrile / 6 h / 20 °C / Inert atmosphere

6: pyridine / 24 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; potassium osmate(VI) dihydrate; sodium periodate; hydrogen fluoride; water; sodium hydrogencarbonate; sodium carbonate; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; water; acetonitrile; 1: Staudinger reaction;
DOI:10.1039/c2ob25793a

Reference yield:

: 1392477-01-8
(2S,3R,4S,5S,6E)-4-amino-N-benzyloxycarbonyl-2-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-6-octene-2,3,5-triol

: 1392477-15-4
1,2,4-tri-O-acetyl-3-amino-N-benzyloxycarbonyl-3,6-dideoxy-β-L-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-dimethylpyridine; sodium periodate; potassium osmate(VI) dihydrate / 1,4-dioxane; water / 2 h / 20 °C

2: sodium carbonate / methanol / 36 h / 20 °C / Inert atmosphere

3: hydrogen fluoride / acetonitrile / 6 h / 20 °C / Inert atmosphere

4: pyridine / 24 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; potassium osmate(VI) dihydrate; sodium periodate; hydrogen fluoride; sodium carbonate; In 1,4-dioxane; methanol; water; acetonitrile;
DOI:10.1039/c2ob25793a