3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride

Base Information

Chemical Name:3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride
CAS No.:304453-34-7
Molecular Formula:C₂₈H₂₀Cl₂FNO₈
Molecular Weight:588.373
Hs Code.:

Synonyms:3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride

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Chemical Property of 3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride

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Technology Process of 3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride

There total 7 articles about 3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride 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: 48.0%

: 304453-32-5
3,4-di-O-benzoyl-6-O-[(tert-butyl)dimethylsilyl]-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride

: 304453-34-7
3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 20 ℃; for 0.666667h;
DOI:10.1002/1522-2675(20000809)83:8<1901::AID-HLCA1901>3.0.CO;2-Q

Reference yield:

: 98-88-4
benzoyl chloride

: 304453-34-7
3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride

Guidance literature:: Multi-step reaction with 3 steps

1: 99.4 percent / DMAP; pyridine / CH₂Cl₂ / 12 h / 20 °C

2: 92 percent / (diethylamino)sulfur trifluoride; NBS / CH₂Cl₂ / 5 h / 20 °C

3: 48 percent / 46 percent aq. HF / acetonitrile / 0.67 h / 20 °C

With pyridine; dmap; N-Bromosuccinimide; diethylamino-sulfur trifluoride; hydrogen fluoride; In dichloromethane; acetonitrile; 1: Acylation / 2: Fluorination / 3: Substitution;
DOI:10.1002/1522-2675(20000809)83:8<1901::AID-HLCA1901>3.0.CO;2-Q

Reference yield:

: 175229-70-6,308796-43-2
1-acetoxy-3,4,6-tri-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside

: 304453-34-7
3,4-di-O-benzoyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranosyl fluoride

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / BF₃*OEt₂ / CH₂Cl₂ / 24 h / 20 °C

2: NaOMe / methanol; CH₂Cl₂ / 0.5 h / 20 °C

3: 1H-imidazole / dimethylformamide / 5 h / 20 °C

4: 99.4 percent / DMAP; pyridine / CH₂Cl₂ / 12 h / 20 °C

5: 92 percent / (diethylamino)sulfur trifluoride; NBS / CH₂Cl₂ / 5 h / 20 °C

6: 48 percent / 46 percent aq. HF / acetonitrile / 0.67 h / 20 °C

With pyridine; 1H-imidazole; dmap; N-Bromosuccinimide; diethylamino-sulfur trifluoride; boron trifluoride diethyl etherate; hydrogen fluoride; sodium methylate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Hydrolysis / 3: Etherification / 4: Acylation / 5: Fluorination / 6: Substitution;
DOI:10.1002/1522-2675(20000809)83:8<1901::AID-HLCA1901>3.0.CO;2-Q