phenyl 2,3-di-O-acetyl-4-deoxy-4-fluoro-5{2H}-β-D-glucopyranosiduronic acid

Base Information

Chemical Name:phenyl 2,3-di-O-acetyl-4-deoxy-4-fluoro-5{2H}-β-D-glucopyranosiduronic acid
CAS No.:461026-37-9
Molecular Formula:C₁₆H₁₇FO₈
Molecular Weight:357.297
Hs Code.:

Synonyms:phenyl 2,3-di-O-acetyl-4-deoxy-4-fluoro-5{2H}-β-D-glucopyranosiduronic acid

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Chemical Property of phenyl 2,3-di-O-acetyl-4-deoxy-4-fluoro-5{2H}-β-D-glucopyranosiduronic acid

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Technology Process of phenyl 2,3-di-O-acetyl-4-deoxy-4-fluoro-5{2H}-β-D-glucopyranosiduronic acid

There total 11 articles about phenyl 2,3-di-O-acetyl-4-deoxy-4-fluoro-5{2H}-β-D-glucopyranosiduronic acid 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: 5.0%

: 461026-36-8
phenyl 2,3-di-O-acetyl-5-bromo-4-deoxy-4-fluoro-β-D-glucopyranosiduronic acid

: 461026-37-9
phenyl 2,3-di-O-acetyl-4-deoxy-4-fluoro-5{2H}-β-D-glucopyranosiduronic acid

Guidance literature:: With tributyltin deuteride; In toluene; for 1.5h; Heating;
DOI:10.1021/ja020627c

Reference yield:

: 25878-60-8
D-galactose pentaacetate

: 461026-37-9
phenyl 2,3-di-O-acetyl-4-deoxy-4-fluoro-5{2H}-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 10 steps

1: HBr; AcOH / CH₂Cl₂ / 0 - 20 °C

2: 40 percent / tetrabutylammonium hydrogensulfate; NaOH / CH₂Cl₂; H₂O

3: 96 percent / NaOMe; MeOH / 20 °C

4: 28 percent / pyridine / -40 - 20 °C

5: 83 percent / methyl diethylaminosulfur trifluoride / CH₂Cl₂ / -30 - 20 °C

6: 85 percent / NaOMe; MeOH / 20 °C

7: 40 percent / 2,2,6,6-tetramethyl-1-piperidinyloxyl; tert-butyl hypochlorite; NaOH / H₂O / 2.5 h / 20 °C / pH 10 - 10.5

8: 79 percent / pyridine / 1.5 h / 20 °C

9: 39 percent / N-bromosuccinimide / CCl₄ / 1 h / Heating; irradiation

10: 5 percent / tributyltin deuteride / toluene / 1.5 h / Heating

With pyridine; methanol; sodium hydroxide; N-Bromosuccinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite; methyl diethylaminosulfur trifluoride; hydrogen bromide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; tributyltin deuteride; acetic acid; In tetrachloromethane; dichloromethane; water; toluene; 2: Koenigs-Knorr reaction / 3: Zemplen deacetylation / 6: Zemplen deacetylation;
DOI:10.1021/ja020627c

Reference yield:

: 2818-58-8
phenyl-β-D-galactopyranoside

: 461026-37-9
phenyl 2,3-di-O-acetyl-4-deoxy-4-fluoro-5{2H}-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 28 percent / pyridine / -40 - 20 °C

2: 83 percent / methyl diethylaminosulfur trifluoride / CH₂Cl₂ / -30 - 20 °C

3: 85 percent / NaOMe; MeOH / 20 °C

4: 40 percent / 2,2,6,6-tetramethyl-1-piperidinyloxyl; tert-butyl hypochlorite; NaOH / H₂O / 2.5 h / 20 °C / pH 10 - 10.5

5: 79 percent / pyridine / 1.5 h / 20 °C

6: 39 percent / N-bromosuccinimide / CCl₄ / 1 h / Heating; irradiation

7: 5 percent / tributyltin deuteride / toluene / 1.5 h / Heating

With pyridine; methanol; sodium hydroxide; N-Bromosuccinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite; methyl diethylaminosulfur trifluoride; sodium methylate; tributyltin deuteride; In tetrachloromethane; dichloromethane; water; toluene; 3: Zemplen deacetylation;
DOI:10.1021/ja020627c