benzyl 2,6-dideoxy-2-(eicosanoylamino)-3-O--6-(octanoylamino)-5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Base Information

Chemical Name:benzyl 2,6-dideoxy-2-(eicosanoylamino)-3-O--6-(octanoylamino)-5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside
CAS No.:82816-58-8
Molecular Formula:C₅₀H₈₆N₂O₉
Molecular Weight:859.241
Hs Code.:

benzyl 2,6-dideoxy-2-(eicosanoylamino)-3-O-<D-1-(methoxycarbonyl)ethyl>-6-(octanoylamino)-5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

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Chemical Property of benzyl 2,6-dideoxy-2-(eicosanoylamino)-3-O--6-(octanoylamino)-5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Chemical Property:

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Technology Process of benzyl 2,6-dideoxy-2-(eicosanoylamino)-3-O--6-(octanoylamino)-5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

There total 9 articles about benzyl 2,6-dideoxy-2-(eicosanoylamino)-3-O--6-(octanoylamino)-5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside 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: 88.0%

: 69888-87-5
N-(eicosanoyloxy)succinimide

: 82816-64-6
(R)-2-{(2R,3R,4R,5R)-4-Amino-5-benzyloxy-2-[(R)-2-octanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid methyl ester

: 82816-58-8
benzyl 2,6-dideoxy-2-(eicosanoylamino)-3-O--6-(octanoylamino)-5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Guidance literature:: In 1,4-dioxane; for 8h; Ambient temperature;
DOI:10.1016/S0008-6215(00)80687-4

Reference yield:

: 81148-68-7
benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside

: 82816-58-8
benzyl 2,6-dideoxy-2-(eicosanoylamino)-3-O--6-(octanoylamino)-5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / pyridine / 5 h / -10 °C

2: 96 percent / 1.) p-toluenesulfonic acid monohydrate; 2.) Amberlite IR-45 (OH^-) ion-exchange resin / dioxane / 3 h / Ambient temperature

3: 87 percent / sodium azide / dimethylformamide / 15 h / 80 °C / Heating

4: Raney Ni (W-1) / ethanol / 1.5 h / Ambient temperature

5: dioxane / 5 h / Ambient temperature

6: hydrogen / 10 percent Pd-C / ethanol / 1 h / Ambient temperature

7: 88 percent / dioxane / 8 h / Ambient temperature

With pyridine; sodium azide; Amberlite IR-45 (OH^-) ion-exchange resin; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; Raney Ni (W-1); In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)80687-4

Reference yield:

: 80134-60-7
benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside

: 82816-58-8
benzyl 2,6-dideoxy-2-(eicosanoylamino)-3-O--6-(octanoylamino)-5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / 60 percent acetic acid / H₂O / 2 h / 45 °C / Heating

2: 89 percent / pyridine / 5 h / -10 °C

3: 96 percent / 1.) p-toluenesulfonic acid monohydrate; 2.) Amberlite IR-45 (OH^-) ion-exchange resin / dioxane / 3 h / Ambient temperature

4: 87 percent / sodium azide / dimethylformamide / 15 h / 80 °C / Heating

5: Raney Ni (W-1) / ethanol / 1.5 h / Ambient temperature

6: dioxane / 5 h / Ambient temperature

7: hydrogen / 10 percent Pd-C / ethanol / 1 h / Ambient temperature

8: 88 percent / dioxane / 8 h / Ambient temperature

With pyridine; sodium azide; Amberlite IR-45 (OH^-) ion-exchange resin; hydrogen; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; Raney Ni (W-1); In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)80687-4