phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-O-p-methoxybenzyl-α-D-glucopyranoside

Base Information

Chemical Name:phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-O-p-methoxybenzyl-α-D-glucopyranoside
CAS No.:1394857-36-3
Molecular Formula:C₃₄H₃₃N₃O₆S
Molecular Weight:611.719
Hs Code.:

Synonyms:phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-O-p-methoxybenzyl-α-D-glucopyranoside

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Chemical Property of phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-O-p-methoxybenzyl-α-D-glucopyranoside

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Technology Process of phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-O-p-methoxybenzyl-α-D-glucopyranoside

There total 6 articles about phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-O-p-methoxybenzyl-α-D-glucopyranoside 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:

: 2-azido-2-deoxy-D-glucose

: 1394857-36-3
phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-O-p-methoxybenzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 144 h / 20 °C / Cooling with ice

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 144 h / 20 °C / Inert atmosphere

3: methanol; sodium / 1.5 h / Inert atmosphere

4: camphorsulfonic acid / acetonitrile / 16 h

5: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5.5 h / Inert atmosphere

6: borane-THF; di-n-butylboryl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 0 °C

7: dmap; pyridine / dichloromethane / 4 h

With pyridine; methanol; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; camphorsulfonic acid; sodium; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1021/jo300722y

Reference yield:

: phenyl 2-azido-2-deoxy-1-thio-α-D-glucopyranoside

: 1394857-36-3
phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-O-p-methoxybenzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: camphorsulfonic acid / acetonitrile / 16 h

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5.5 h / Inert atmosphere

3: borane-THF; di-n-butylboryl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 0 °C

4: dmap; pyridine / dichloromethane / 4 h

With pyridine; dmap; borane-THF; di-n-butylboryl trifluoromethanesulfonate; camphorsulfonic acid; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1021/jo300722y

Reference yield:

: 1078691-95-8
(+)-D-glucosamine hydrochloride

: 1394857-36-3
phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-O-p-methoxybenzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate / methanol / 4 h / 20 °C

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 144 h / 20 °C / Cooling with ice

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 144 h / 20 °C / Inert atmosphere

4: methanol; sodium / 1.5 h / Inert atmosphere

5: camphorsulfonic acid / acetonitrile / 16 h

6: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5.5 h / Inert atmosphere

7: borane-THF; di-n-butylboryl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 0 °C

8: dmap; pyridine / dichloromethane / 4 h

With pyridine; methanol; dmap; imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; borane-THF; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; camphorsulfonic acid; sodium; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1021/jo300722y