dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-manno-heptopyranosyl) phosphate

Base Information

• Chemical Name: dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-manno-heptopyranosyl) phosphate
• CAS No.: 651731-05-4
• Molecular Formula: C₃₁H₃₇O₁₅P
• Molecular Weight: 680.6

Synonyms:dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-manno-heptopyranosyl) phosphate

Chemical Property of dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-manno-heptopyranosyl) phosphate

Chemical Property:

Purity/Quality:

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Technology Process of dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-manno-heptopyranosyl) phosphate

There total 4 articles about dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-manno-heptopyranosyl) 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: 65.0%

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) + (2R,3R,4S,5S)-2-((R)-1,2-diacetoxyethyl)-6-hydroxytetrahydro-2H-pyran-3,4,5-triyl triacetate → dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-manno-heptopyranosyl) phosphate (651731-05-4) + dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-β-D-manno-heptopyranosyl) phosphate (651731-07-6)

Guidance literature:

Dibenzyl N,N-diisopropylphosphoramidite; (2R,3R,4S,5S)-2-((R)-1,2-diacetoxyethyl)-6-hydroxytetrahydro-2H-pyran-3,4,5-triyl triacetate; With 1H-tetrazole; In dichloromethane; acetonitrile; at 20 ℃; for 2h;

With tert.-butylhydroperoxide; In dichloromethane; acetonitrile; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.carres.2003.09.012

Reference yield: 58.0%

dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-D-manno-heptopyranosyl)phosphite → dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-manno-heptopyranosyl) phosphate (651731-05-4) + dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-β-D-manno-heptopyranosyl) phosphate (651731-07-6)

Guidance literature:

With tert.-butylhydroperoxide; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0008-6215(03)00319-7

Reference yield:

D-glycero-D-manno-heptopyranose hexa-acetate (130404-55-6) → dibenzyl (2,3,4,6,7-penta-O-acetyl-D-glycero-α-D-manno-heptopyranosyl) phosphate (651731-05-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / N,N-diisopropylethylamine; ammonium acetate / dimethylformamide

2: 4-N,N-dimethylaminopyridine / CH₂Cl₂; acetonitrile / 2 h / 20 °C

3: 58 percent / tert-BuOOH / CH₂Cl₂ / 3 h / 20 °C

With ammonium acetate; tert.-butylhydroperoxide; dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0008-6215(03)00319-7

upstream raw materials:

Dibenzyl N,N-diisopropylphosphoramidite

D-glycero-D-manno-heptopyranose hexa-acetate

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