3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl fluoride

Base Information

Chemical Name:3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl fluoride
CAS No.:304453-42-7
Molecular Formula:C₂₆H₂₄Cl₂FNO₉
Molecular Weight:584.382
Hs Code.:

Synonyms:3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl fluoride

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Chemical Property of 3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl fluoride

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Technology Process of 3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl fluoride

There total 8 articles about 3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(4-methoxybenzyl)-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: 93.0%

: 304453-40-5
dodecyl 3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside

: 304453-42-7
3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl fluoride

Guidance literature:: With N-Bromosuccinimide; diethylamino-sulfur trifluoride; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1002/1522-2675(20000809)83:8<1901::AID-HLCA1901>3.0.CO;2-Q

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 304453-42-7
3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl fluoride

Guidance literature:: Multi-step reaction with 5 steps

1: CSA / dimethylformamide / 5 h / 20 °C / 20 Torr

2: DMAP; pyridine / dimethylformamide / 12 h / 20 °C

3: 80 percent / NaBH₃CN; Me₃SiCl; 3 Angstroem molecular sieves / tetrahydrofuran; acetonitrile / 2 h / 0 °C

4: 99 percent / DMAP; pyridine / CH₂Cl₂ / 3 h / 20 °C

5: 93 percent / (diethylamino)sulfur trifluoride; NBS / CH₂Cl₂ / 5 h / 20 °C

With pyridine; dmap; N-Bromosuccinimide; chloro-trimethyl-silane; diethylamino-sulfur trifluoride; 3 A molecular sieve; camphor-10-sulfonic acid; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Acetylation / 3: Reduction / 4: Acetylation / 5: Fluorination;
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

: 304453-42-7
3,6-di-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl fluoride

Guidance literature:: Multi-step reaction with 7 steps

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

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

3: CSA / dimethylformamide / 5 h / 20 °C / 20 Torr

4: DMAP; pyridine / dimethylformamide / 12 h / 20 °C

5: 80 percent / NaBH₃CN; Me₃SiCl; 3 Angstroem molecular sieves / tetrahydrofuran; acetonitrile / 2 h / 0 °C

6: 99 percent / DMAP; pyridine / CH₂Cl₂ / 3 h / 20 °C

7: 93 percent / (diethylamino)sulfur trifluoride; NBS / CH₂Cl₂ / 5 h / 20 °C

With pyridine; dmap; N-Bromosuccinimide; chloro-trimethyl-silane; diethylamino-sulfur trifluoride; 3 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium cyanoborohydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Hydrolysis / 3: Condensation / 4: Acetylation / 5: Reduction / 6: Acetylation / 7: Fluorination;
DOI:10.1002/1522-2675(20000809)83:8<1901::AID-HLCA1901>3.0.CO;2-Q