ethyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

Base Information

Chemical Name:ethyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside
CAS No.:263758-88-9
Molecular Formula:C₄₁H₄₃N₃O₁₅S
Molecular Weight:849.87
Hs Code.:

Synonyms:ethyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

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Chemical Property of ethyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

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Technology Process of ethyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

There total 5 articles about ethyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-1-thio-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: 86.0%

: 67817-15-6
Acetic acid (2R,3S,4R,5R,6R)-4-acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yl ester

: 213743-11-4
ethyl 2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

: 263758-88-9
ethyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

Guidance literature:: With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -35 ℃; for 2h;
DOI:10.1080/07328300008544063

Reference yield:

: 98-88-4
benzoyl chloride

: 263758-88-9
ethyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: pTsOH / 2 h / 20 °C

1.2: 76 percent / pyridine / 3 h / 20 °C

2.1: 80 percent / TFA / 0.25 h / 20 °C

3.1: Bu₂SnO / methanol / 2.5 h / Heating

3.2: 86 percent / triethylamine / tetrahydrofuran / 3 h / 20 °C

4.1: 86 percent / sym-collidine; AgOTf; powdered 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -35 °C

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; trifluoroacetic acid; In methanol; dichloromethane; 1.1: cyclocondensation / 1.2: Acylation / 2.1: Hydrolysis / 3.1: complexation / 3.2: Acylation / 4.1: glycosylation;
DOI:10.1080/07328300008544063

Reference yield:

: 194858-02-1
ethyl 2,6-di-O-benzoyl-1-thio-β-D-galactopyranoside

: 263758-88-9
ethyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: Bu₂SnO / methanol / 2.5 h / Heating

1.2: 86 percent / triethylamine / tetrahydrofuran / 3 h / 20 °C

2.1: 86 percent / sym-collidine; AgOTf; powdered 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -35 °C

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; In methanol; dichloromethane; 1.1: complexation / 1.2: Acylation / 2.1: glycosylation;
DOI:10.1080/07328300008544063