4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride

Base Information

• Chemical Name: 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride
• CAS No.: 303153-45-9
• Molecular Formula: C₂₄H₂₈FN₃O₁₁
• Molecular Weight: 553.498
• Mol file: 303153-45-9.mol

Synonyms:4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride

Chemical Property of 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride

There total 10 articles about 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl 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: 67.0%

4-azido-2-O-benzoyl-4,6-dideoxy-α-D-galactopyranosyl fluoride (303153-48-2) + (2S,3R,4S,5R)-2-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (52544-91-9,52544-92-0,62774-34-9,98461-49-5,107961-02-4,107961-33-1,110221-83-5) → 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-β-D-galactopyranosyl + 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride (303153-45-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at -78 - -40 ℃;

DOI:10.1002/chem.200700863

Reference yield:

4-azido-2-O-benzoyl-4,6-dideoxy-α-D-galactopyranosyl fluoride (303153-48-2) + (2S,3R,4S,5R)-2-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (52544-91-9,52544-92-0,62774-34-9,98461-49-5,107961-02-4,107961-33-1,110221-83-5) → 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride (303153-45-9) + Benzoic acid (2R,3R,4S,5S,6R)-5-azido-2-fluoro-6-methyl-4-((2R,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -40 ℃; for 2h;

DOI:10.1016/S0040-4039(00)01153-9

Reference yield:

methyl 2,3-di-O-acetyl-4,6-di-O-mesyl-α-D-glucopyranoside (22435-34-3) → 4-azido-2-O-benzoyl-4,6-dideoxy-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-galactopyranosyl fluoride (303153-45-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / NaI / butan-2-one / 6 h / Heating

2: 95 percent / H₂; NaOAc / ethanol; ethyl acetate / 15 h

3: 87 percent / NaN₃; n-Bu₄NCl / dimethylformamide / 10 h / 110 °C

4: 91 percent / conc. H₂SO₄ / 4 h

5: (HF)n*pyridine / CH₂Cl₂ / 8 h / -20 - 20 °C

6: K₂CO₃ / methanol / 1 h / 0 °C

7: 50 percent / pyridine / 15 h / 0 - 20 °C

8: NIS; TfOH / CH₂Cl₂ / 2 h / -40 °C

With N-iodo-succinimide; sodium azide; trifluorormethanesulfonic acid; (HF)n*pyridine; sulfuric acid; tetrabutyl-ammonium chloride; hydrogen; sodium acetate; potassium carbonate; sodium iodide; In pyridine; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; butanone; 1: Substitution / 2: Dehydroiodination / 3: Substitution / 4: Acetylation / 5: Substitution / 6: Deacetylation / 7: benzoylation / 8: glycosylation;

DOI:10.1016/S0040-4039(00)01153-9

upstream raw materials:

4-azido-2-O-benzoyl-4,6-dideoxy-α-D-galactopyranosyl fluoride

(2S,3R,4S,5R)-2-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

methyl 2,3-di-O-acetyl-4,6-di-O-mesyl-α-D-glucopyranoside

4-azido-4,6-dideoxy-α-D-galactopyranosyl fluoride

Downstream raw materials:

C₆₃H₆₄N₄O₂₇