4-phenyl-1-(4',5',6'-tri-O-benzyl-3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole

Base Information

• Chemical Name: 4-phenyl-1-(4',5',6'-tri-O-benzyl-3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole
• CAS No.: 944478-43-7
• Molecular Formula: C₃₆H₃₇N₃O₅
• Molecular Weight: 591.707

Synonyms:4-phenyl-1-(4',5',6'-tri-O-benzyl-3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole

Chemical Property of 4-phenyl-1-(4',5',6'-tri-O-benzyl-3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole

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Technology Process of 4-phenyl-1-(4',5',6'-tri-O-benzyl-3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole

There total 2 articles about 4-phenyl-1-(4',5',6'-tri-O-benzyl-3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole 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%

4,5,6-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo-septanosyl azide (944478-39-1) + phenylacetylene (536-74-3) → 4-phenyl-1-(4',5',6'-tri-O-benzyl-3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole (944478-43-7)

Guidance literature:

With copper diacetate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20 ℃;

DOI:10.1016/j.carres.2007.03.026

Reference yield:

1,6-anhydro-4,5,7-tri-O-benzyl-2,3-dideoxy-D-glucosept-1-enitol (592497-14-8) → 4-phenyl-1-(4',5',6'-tri-O-benzyl-3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole (944478-43-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMDO / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 22 percent / NaN₃ / dimethylformamide; H₂O / 4 h / 20 °C

2.1: 65 percent / sodium ascorbate; Cu(OAc)2 / H₂O; 2-methyl-propan-2-ol / 20 °C

With copper diacetate; sodium L-ascorbate; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/j.carres.2007.03.026

Reference yield: 98.0%

4-phenyl-1-(4',5',6'-tri-O-benzyl-3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole (944478-43-7) → 4-phenyl-1-(3'-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 4h;

DOI:10.1016/j.carres.2007.03.026

upstream raw materials:

4,5,6-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo-septanosyl azide

phenylacetylene

1,6-anhydro-4,5,7-tri-O-benzyl-2,3-dideoxy-D-glucosept-1-enitol

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