p-tolyl 2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-1-thio-α-L-idopyranoside

Base Information

• Chemical Name: p-tolyl 2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-1-thio-α-L-idopyranoside
• CAS No.: 1415218-19-7
• Molecular Formula: C₆₁H₆₇N₃O₁₂SSi
• Molecular Weight: 1094.37

Synonyms:p-tolyl 2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-1-thio-α-L-idopyranoside

Chemical Property of p-tolyl 2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-1-thio-α-L-idopyranoside

Chemical Property:

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Technology Process of p-tolyl 2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-1-thio-α-L-idopyranoside

There total 7 articles about p-tolyl 2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-1-thio-α-L-idopyranoside 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: 93.0%

p-tolyl-2-azido-3-O-benzyl-4-O-t-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-1-thio-α-L-idopyranoside (1415218-18-6) + tert-butylchlorodiphenylsilane (58479-61-1) → p-tolyl 2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-1-thio-α-L-idopyranoside (1415218-19-7)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201205601

Reference yield:

p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside (1242437-13-3) → p-tolyl 2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-1-thio-α-L-idopyranoside (1415218-19-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: silver trifluoromethanesulfonate / dichloromethane; diethyl ether / 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

1.2: 0.08 h / -78 °C / Inert atmosphere

1.3: 2 h / -78 - 0 °C / Inert atmosphere

2.1: magnesium methanolate / dichloromethane; methanol / -20 - 0 °C / Inert atmosphere

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / Inert atmosphere

5.1: pyridine hydrogenfluoride / 0 °C / Inert atmosphere

6.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; silver trifluoromethanesulfonate; pyridine hydrogenfluoride; magnesium methanolate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1002/anie.201205601

Reference yield:

p-tolyl 2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-α-L-idopyranoside (1242437-11-1) → p-tolyl 2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-1-thio-α-L-idopyranoside (1415218-19-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: silver trifluoromethanesulfonate / dichloromethane; diethyl ether / 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

1.2: 0.08 h / -78 °C / Inert atmosphere

1.3: 2 h / -78 - 0 °C / Inert atmosphere

2.1: magnesium methanolate / dichloromethane; methanol / -20 - 0 °C / Inert atmosphere

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / Inert atmosphere

5.1: pyridine hydrogenfluoride / 0 °C / Inert atmosphere

6.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; silver trifluoromethanesulfonate; pyridine hydrogenfluoride; magnesium methanolate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1002/anie.201205601

upstream raw materials:

p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside

p-tolyl 2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-α-L-idopyranoside

p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-α-L-idopyranoside

p-tolyl 2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-α-L-idopyranoside

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