3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose
• CAS No.: 99194-76-0
• Molecular Formula: C₂₀H₂₅NO₁₀
• Molecular Weight: 439.419

Synonyms:3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose

Chemical Property of 3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose

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Technology Process of 3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose

There total 23 articles about 3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose 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%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(benzyloxycarbonyl)amino-α/β-D-glucopyranoside (5348-99-2,35946-66-8,82264-19-5,100483-05-4) → 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranose (99194-76-0,140183-53-5)

Guidance literature:

With benzylamine; In tetrahydrofuran; for 15h; Inert atmosphere;

DOI:10.1002/ejoc.201301015

Reference yield: 94.0%

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate (35946-66-8) → 3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose (99194-76-0)

Guidance literature:

With acetic acid; hydrazine; In tetrahydrofuran;

DOI:10.1002/anie.200460388

Reference yield: 94.0%

3,4,6-tri-O-acetyl-2-(benzoyloxycarbonyl)amino-2-deoxy-α-D-glucopyranosyl bromide (73446-41-0) → 3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose (99194-76-0)

Guidance literature:

With water; silver carbonate; In acetone; at 0 ℃;

DOI:10.1248/cpb.34.3733

upstream raw materials:

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate

D-glucosamine hydrochloride

benzyl ((2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

benzyl chloroformate

Downstream raw materials:

2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime

C₂₂H₂₅Cl₃N₂O₁₀

tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside

TBDMS 2-deoxy-2-(N-benzyloxycarbonylamino)-β-D-glucopyranoside

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