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

Base Information

Chemical Name:benzyl 6-azido-2-(benzyloxycarbonylamino)-2,6-dideoxy-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside
CAS No.:81161-20-8
Molecular Formula:C₃₀H₃₈N₄O₉
Molecular Weight:598.653
Hs Code.:

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

Synonyms:benzyl 6-azido-2-(benzyloxycarbonylamino)-2,6-dideoxy-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

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

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

There total 5 articles about benzyl 6-azido-2-(benzyloxycarbonylamino)-2,6-dideoxy-3-O--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: 87.0%

: 81161-19-5
benzyl 2-(benzyloxycarbonylamino)-2-deoxy-6-O-mesyl-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

: 81161-20-8
benzyl 6-azido-2-(benzyloxycarbonylamino)-2,6-dideoxy-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 15h; Heating;
DOI:10.1016/S0008-6215(00)80687-4

Reference yield:

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

: 81161-20-8
benzyl 6-azido-2-(benzyloxycarbonylamino)-2,6-dideoxy-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Guidance literature:: Multi-step reaction with 3 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

With pyridine; sodium azide; Amberlite IR-45 (OH^-) ion-exchange resin; toluene-4-sulfonic acid; In 1,4-dioxane; 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

: 81161-20-8
benzyl 6-azido-2-(benzyloxycarbonylamino)-2,6-dideoxy-3-O--5-O-(tetrahydropyran-2-yl)-β-D-glucofuranoside

Guidance literature:: Multi-step reaction with 4 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

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