dibenzyl (3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)phosphate

Base Information

• Chemical Name: dibenzyl (3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)phosphate
• CAS No.: 209005-11-8
• Molecular Formula: C₂₆H₃₀FO₁₁P
• Molecular Weight: 568.49
• Mol file: 209005-11-8.mol

Synonyms:dibenzyl (3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)phosphate

Chemical Property of dibenzyl (3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzyl (3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)phosphate

There total 10 articles about dibenzyl (3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)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: 79.0%

phosphoric acid dibenzyl ester (1623-08-1) + 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl bromide (801291-55-4) → dibenzyl (3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)phosphate (209005-11-8) + 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranose (226382-72-5)

Guidance literature:

With silver carbonate; In toluene; Inert atmosphere; Darkness;

DOI:10.1039/c4ob00235k

Reference yield:

2-deoxy-D-arabino-hexopyranose (61-58-5,13299-15-5,13299-16-6,14215-77-1,14215-78-2,20789-85-9,23568-30-1,25494-04-6,34339-39-4,34339-40-7,34339-46-3,34339-47-4,114717-20-3,114717-21-4,137491-75-9,137491-76-0) → dibenzyl (3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)phosphate (209005-11-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / 18 h / 20 °C / Inert atmosphere

2.1: hydrogen bromide / dichloromethane / 96 h / 20 °C / Inert atmosphere

3.1: 1-methyl-1H-imidazole; zinc / ethyl acetate / 18 h / Reflux; Inert atmosphere

4.1: Selectfluor; water / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

4.2: 20 h / 20 °C / Inert atmosphere

5.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 16 h / 20 - 50 °C / Inert atmosphere

6.1: 4,5-dicyano-1H-imidazole / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

7.1: 3-chloro-benzenecarboperoxoic acid / 4 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1-methyl-1H-imidazole; 4,5-dicyano-1H-imidazole; Selectfluor; water; hydrogen bromide; hydrazinium monoacetate; 3-chloro-benzenecarboperoxoic acid; zinc; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201100906

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose (69515-91-9) → dibenzyl (3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranosyl)phosphate (209005-11-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogen bromide / dichloromethane / 96 h / 20 °C / Inert atmosphere

2.1: 1-methyl-1H-imidazole; zinc / ethyl acetate / 18 h / Reflux; Inert atmosphere

3.1: Selectfluor; water / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

3.2: 20 h / 20 °C / Inert atmosphere

4.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 16 h / 20 - 50 °C / Inert atmosphere

5.1: 4,5-dicyano-1H-imidazole / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / 4 h / 0 - 20 °C / Inert atmosphere

With 1-methyl-1H-imidazole; 4,5-dicyano-1H-imidazole; Selectfluor; water; hydrogen bromide; hydrazinium monoacetate; 3-chloro-benzenecarboperoxoic acid; zinc; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201100906

upstream raw materials:

2-deoxy-D-arabino-hexopyranose

1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose

1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranoside

Dibenzyl N,N-diisopropylphosphoramidite

Downstream raw materials:

dibenzyl (2-deoxy-2-fluoro-α-D-mannopyranosyl)phosphate

Refernces

• 1、 Wolf, Saskia,Berrio, Rosmirt Molina,Meier, Chris. "Synthesis of nonnatural nucleoside diphosphate sugars". . p. 6304 - 6313. Retrieved 2011/12/16.