methyl 5-acetamido-2,3-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate

Base Information

• Chemical Name: methyl 5-acetamido-2,3-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate
• CAS No.: 134258-01-8
• Molecular Formula: C₄₀H₄₃NO₉
• Molecular Weight: 681.783

Synonyms:methyl 5-acetamido-2,3-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate

Chemical Property of methyl 5-acetamido-2,3-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate

Chemical Property:

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Technology Process of methyl 5-acetamido-2,3-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate

There total 2 articles about methyl 5-acetamido-2,3-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate 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: 85.0%

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3-bromo-3,5-dideoxy-β-D-erythro-L-manno-2-nonulopyranosonate (129234-78-2) → methyl 5-acetamido-2,3-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate (134258-01-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 0.166667h; Ambient temperature;

DOI:10.1002/hlca.19910740223

Reference yield:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (116096-63-0) → methyl 5-acetamido-2,3-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate (134258-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / NBS / acetonitrile; H₂O / 0.33 h / 70 °C

2: 85 percent / DBU / acetonitrile / 0.17 h / Ambient temperature

With N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; acetonitrile;

DOI:10.1002/hlca.19910740223

Reference yield: 96.0%

methyl 5-acetamido-2,3-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate (134258-01-8) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2-bromo-2,5-dideoxy-β-D-erythro-L-gluco-2-nonulopyranosonate (134258-02-9)

Guidance literature:

With titanium(IV) bromide; In tetrahydrofuran; at -70 ℃; for 0.166667h;

DOI:10.1002/hlca.19910740223

upstream raw materials:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3-bromo-3,5-dideoxy-β-D-erythro-L-manno-2-nonulopyranosonate

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Downstream raw materials:

methyl 5-acetamido-2,7-anhydro-4,8,9-tri-O-benzyl-5-deoxy-β-D-erythro-L-gluco-2-nonulopyranosonate

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2-bromo-2,5-dideoxy-β-D-erythro-L-gluco-2-nonulopyranosonate

methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate

methyl 5-acetamido-2,6-anhydro-3,4,7,8,9-penta-O-benzyl-5-deoxy-D-arabino-L-gulo-2-nononate

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