tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Base Information

• Chemical Name: tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside
• CAS No.: 1235137-43-5
• Molecular Formula: C₅₄H₅₅N₃O₉S
• Molecular Weight: 922.111

Synonyms:tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property of tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

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Technology Process of tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

There total 9 articles about tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-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: 65.0%

tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (905704-43-0) + 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl trichloroacetimidate → tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (1235137-43-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -50 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1002/asia.200900765

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (1235137-43-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: imidazole-1-sulfonyl azide hydrochloride; copper(II) sulfate; triethylamine / methanol / 20 °C

2.1: pyridine / 10 h / 20 °C

3.1: boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C / Inert atmosphere

4.1: sodium / methanol; dichloromethane / 3 h / 20 °C

5.1: toluene-4-sulfonic acid / acetonitrile / 4 h / 20 °C

6.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

7.1: triethylsilane / dichloromethane / 0.33 h / -15 - 20 °C / Molecular sieve; Inert atmosphere

7.2: 2 h / -15 °C / Molecular sieve; Inert atmosphere

8.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -50 °C / Molecular sieve; Inert atmosphere

With pyridine; triethylsilane; imidazole-1-sulfonyl azide hydrochloride; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium; sodium hydride; toluene-4-sulfonic acid; copper(II) sulfate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/asia.200900765

Reference yield:

C20H21N3O4S → tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (1235137-43-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

2.1: triethylsilane / dichloromethane / 0.33 h / -15 - 20 °C / Molecular sieve; Inert atmosphere

2.2: 2 h / -15 °C / Molecular sieve; Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -50 °C / Molecular sieve; Inert atmosphere

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/asia.200900765

upstream raw materials:

4-methylphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α,β-D-glucopyranoside

tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

(+)-D-glucosamine hydrochloride

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

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