5-Acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nononic acid

Base Information

• Chemical Name: 5-Acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nononic acid
• CAS No.: 131292-44-9
• Molecular Formula: C₃₉H₄₃NO₈
• Molecular Weight: 653.772

Synonyms:5-Acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nononic acid

Chemical Property of 5-Acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nononic acid

Chemical Property:

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Technology Process of 5-Acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nononic acid

There total 1 articles about 5-Acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nononic acid 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: 100.0%

Methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nonanonate (131318-23-5) → 5-Acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nononic acid (131292-44-9)

Guidance literature:

With sodium hydroxide; In methanol; for 1h; Ambient temperature;

DOI:10.1002/hlca.19900730523

Reference yield:

5-Acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nononic acid (131292-44-9) → tert-Butyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-manno-nononate (131318-25-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) (COCl)2 2) pyridine / 1) CH₂Cl₂, DMF, 30 min, 0 deg C 2) 12h, r.t.

2: BuLi, N-cyclohexylisopropylamine / tetrahydrofuran / 3 h / -50 °C

With pyridine; n-butyllithium; oxalyl dichloride; N-cyclohexylisopropylamine; In tetrahydrofuran;

DOI:10.1002/hlca.19900730523

Reference yield:

lead(IV) tetraacetate (546-67-8) + 5-Acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nononic acid (131292-44-9) → 4-Acetamido-3,6,7,8-tetra-O-benzyl-2,4-dideoxy-D-glycero-α-D-galacto-octopyranosyl acetate (131292-45-0) + 4-Acetamido-3,6,7,8-tetra-O-benzyl-2,4-dideoxy-D-glycero-β-D-galacto-octopyranosyl acetate (131292-46-1)

Guidance literature:

With pyridine; at 60 ℃; for 2.5h; Yield given. Yields of byproduct given;

DOI:10.1002/hlca.19900730523

upstream raw materials:

Methyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nonanonate

Downstream raw materials:

4-Acetamido-3,6,7,8-tetra-O-benzyl-2,4-dideoxy-D-glycero-α-D-galacto-octopyranosyl acetate

4-Acetamido-3,6,7,8-tetra-O-benzyl-2,4-dideoxy-D-glycero-β-D-galacto-octopyranosyl acetate

tert-Butyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-gluco-nononate

tert-Butyl 5-acetamido-2,6-anhydro-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-erythro-L-manno-nononate

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