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

Base Information

Chemical Name:benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosyl)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside
CAS No.:461026-00-6
Molecular Formula:C₂₁H₃₀FNO₁₀
Molecular Weight:475.468
Hs Code.:

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

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

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

There total 18 articles about benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosyl)-(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: 84.0%

: 461025-99-0
benzyl O-(2,3,6-tri-O-benzoyl-4-deoxy-4-fluoro-β-D-glucopyranosyl)-(1->3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-tert-butyldimethylsilyl-β-D-galactopyranoside

: 461026-00-6
benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosyl)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

Guidance literature:: With methanol; sodium methylate; at 20 ℃;
DOI:10.1021/ja020627c

Reference yield:

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

: 461026-00-6
benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosyl)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 8 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

With pyridine; 1H-imidazole; methanol; dmap; tetrabutyl ammonium fluoride; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 8.1: Zemplen deacetylation;
DOI:10.1021/ja020627c

Reference yield:

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

: 461026-00-6
benzyl O-(4-deoxy-4-fluoro-β-D-glucopyranosyl)-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 63 percent / methyl diethylaminosulfur trifluoride / CH₂Cl₂ / -30 - 20 °C

2: 72 percent / HBr; AcOH / CH₂Cl₂ / 15 h / 20 °C

3: 32 percent / silver triflate / CH₂Cl₂ / 4.5 h / 20 °C

4: 84 percent / NaOMe; MeOH / 20 °C

With methanol; methyl diethylaminosulfur trifluoride; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; acetic acid; In dichloromethane; 4: Zemplen deacetylation;
DOI:10.1021/ja020627c