6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-D-glucopyranosyl trichloroacetamidate

Base Information

• Chemical Name: 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-D-glucopyranosyl trichloroacetamidate
• CAS No.: 134221-38-8
• Molecular Formula: C₂₅H₂₇Cl₃N₄O₇
• Molecular Weight: 601.871

Synonyms:6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-D-glucopyranosyl trichloroacetamidate

Chemical Property of 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-D-glucopyranosyl trichloroacetamidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-D-glucopyranosyl trichloroacetamidate

There total 8 articles about 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-D-glucopyranosyl trichloroacetamidate 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:

methyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-1-thio-α,β-glucopyranoside → 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-D-glucopyranosyl trichloroacetamidate (134221-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / NBS, H₂O / CH₂Cl₂ / 3 h / 0 °C

2: K₂CO₃ / CH₂Cl₂ / 3 h / Ambient temperature

With N-Bromosuccinimide; water; potassium carbonate; In dichloromethane;

Reference yield:

2-azido-2-deoxy-D-glucose → 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-D-glucopyranosyl trichloroacetamidate (134221-38-8)

Guidance literature:

Multi-step reaction with 9 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 / 2 h / 0 - 20 °C

8: N-Bromosuccinimide / acetone / 0 °C

9: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / Inert atmosphere

With pyridine; methanol; dmap; N-Bromosuccinimide; borane-THF; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; camphorsulfonic acid; sodium; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil;

DOI:10.1021/jo300722y

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-(p-methoxybenzyl)-D-glucopyranosyl trichloroacetamidate (134221-38-8)

Guidance literature:

Multi-step reaction with 10 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 / 2 h / 0 - 20 °C

9: N-Bromosuccinimide / acetone / 0 °C

10: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / Inert atmosphere

With pyridine; methanol; dmap; imidazole-1-sulfonyl azide hydrochloride; N-Bromosuccinimide; copper(ll) sulfate pentahydrate; borane-THF; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; camphorsulfonic acid; sodium; sodium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil;

DOI:10.1021/jo300722y

upstream raw materials:

(+)-D-glucosamine hydrochloride

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-1-thiol-α-D-glucopyranoside

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

Downstream raw materials:

methyl (phenyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-idopyranoside)-uronate

methyl (phenyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-acetyl-3-O-benzyl-1-thio-α-L-idopyranoside)-uronate

6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-2-O-acetyl-3-O-benzyl-1-O-trichloroacetimidate-α/β-L-idopyranuronate

6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate

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