3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate
• CAS No.: 219564-51-9
• Molecular Formula: C₂₈H₃₁F₃NO₁₂P
• Molecular Weight: 661.523

Synonyms:3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate

Chemical Property of 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate

Chemical Property:

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Technology Process of 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate

There total 7 articles about 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate 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: 59.0%

dibenzyl phosphochloridate (538-37-4) + 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranose (212137-44-5) → 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate (219564-51-9)

Guidance literature:

3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranose; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 0.0333333h;

dibenzyl phosphochloridate; In tetrahydrofuran; hexane; at -60 - -50 ℃; for 0.5h;

DOI:10.1139/V06-043

Reference yield:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(bis-benzyloxy-phosphanyloxy)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester → 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate (219564-51-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -60 - 20 ℃; for 2.5h;

DOI:10.1021/ja0555217

Reference yield:

3,4,6-Tri-O-acetyl-2-trifluoracetamino-2-desoxy-D-glucose (28719-30-4) → 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate (219564-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrazole / CH₂Cl₂ / 1 h / -50 - -10 °C

2: MCPBA / CH₂Cl₂ / 2.5 h / -60 - 20 °C

With 1H-tetrazole; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ja0555217

upstream raw materials:

dibenzyl phosphochloridate

3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranose

2-trifluoroacetamido-2-deoxy-α,β-D-glucopyranose

2-deoxy-2-trifluoroacetamido-1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside

Downstream raw materials:

uridine 5'-(2-amino-2-deoxy-α-D-glucopyranosyl)-diphosphate

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