benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosiduronic acid)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

Base Information

Chemical Name:benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosiduronic acid)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside
CAS No.:461026-01-7
Molecular Formula:C₂₁H₂₈FNO₁₁
Molecular Weight:489.452
Hs Code.:

Synonyms:benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosiduronic acid)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

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Chemical Property of benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosiduronic acid)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

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Technology Process of benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosiduronic acid)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

There total 21 articles about benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosiduronic acid)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside 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:

: (2R,3S,4R,5R,6R)-6-[(2S,4aR,6R,7R,8R,8aR)-7-Acetylamino-6-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3-fluoro-4,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid

: 461026-01-7
benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosiduronic acid)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

Guidance literature:: (2R,3S,4R,5R,6R)-6-[(2S,4aR,6R,7R,8R,8aR)-7-Acetylamino-6-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-3-fluoro-4,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid; In methanol; for 0.25h; Heating;

With acetic acid; In methanol; at 20 ℃; Further stages.;
DOI:10.1021/ja020627c

Reference yield:

: 41355-95-7,347411-88-5
benzyl 2-acetamido-2-deoxy-β-D-galactopyranoside

: 461026-01-7
benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosiduronic acid)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1.1: p-TsOH

1.2: 85 percent / aq. AcOH / methanol / 45 °C

2.1: 99 percent / pyridine / 20 °C

3.1: 80 percent / AcOH / H₂O / 50 °C

4.1: 79 percent / imidazole / dimethylformamide / 2 h / 80 °C

5.1: 95 percent / pyridine; 4-(dimethylamino)pyridine / 1 h / 20 °C

6.1: 28 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

7.1: 32 percent / silver triflate / CH₂Cl₂ / 4.5 h / 20 °C

8.1: 84 percent / NaOMe; MeOH / 20 °C

9.1: 88 percent / p-toluenesulfonic acid monohydrate / 2-methyl-propan-2-ol / 7 h / 50 °C

10.1: 2,2,6,6-tetramethyl-1-piperidinyloxyl; aq. NaOCl; NaBr / TBAB; NaHCO₃ / ethyl acetate / 2.5 h / 0 °C

11.1: methanol / 0.25 h / Heating

11.2: 19 mg / AcOH / methanol / 20 °C

With pyridine; 1H-imidazole; methanol; dmap; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; sodium bromide; tetrabutylammomium bromide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 8.1: Zemplen deacetylation;
DOI:10.1021/ja020627c

Reference yield:

: 114718-46-6
1,2,3,6-tetra-O-benzoyl-α-D-galactopyranose

: 461026-01-7
benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosiduronic acid)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 63 percent / methyl diethylaminosulfur trifluoride / CH₂Cl₂ / -30 - 20 °C

2.1: 72 percent / HBr; AcOH / CH₂Cl₂ / 15 h / 20 °C

3.1: 32 percent / silver triflate / CH₂Cl₂ / 4.5 h / 20 °C

4.1: 84 percent / NaOMe; MeOH / 20 °C

5.1: 88 percent / p-toluenesulfonic acid monohydrate / 2-methyl-propan-2-ol / 7 h / 50 °C

6.1: 2,2,6,6-tetramethyl-1-piperidinyloxyl; aq. NaOCl; NaBr / TBAB; NaHCO₃ / ethyl acetate / 2.5 h / 0 °C

7.1: methanol / 0.25 h / Heating

7.2: 19 mg / AcOH / methanol / 20 °C

With methanol; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; methyl diethylaminosulfur trifluoride; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; sodium bromide; tetrabutylammomium bromide; sodium hydrogencarbonate; In methanol; dichloromethane; ethyl acetate; tert-butyl alcohol; 4.1: Zemplen deacetylation;
DOI:10.1021/ja020627c