6,2',3',6'-tetra-O-benzoylantirrhinoside

Base Information

• Chemical Name: 6,2',3',6'-tetra-O-benzoylantirrhinoside
• CAS No.: 202402-58-2
• Molecular Formula: C₄₃H₃₈O₁₄
• Molecular Weight: 778.766
• Mol file: 202402-58-2.mol

Synonyms:6,2',3',6'-tetra-O-benzoylantirrhinoside

Chemical Property of 6,2',3',6'-tetra-O-benzoylantirrhinoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6,2',3',6'-tetra-O-benzoylantirrhinoside

There total 1 articles about 6,2',3',6'-tetra-O-benzoylantirrhinoside 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: 55.0%

benzoyl chloride (98-88-4) + anthirrinoside (20486-27-5,20770-65-4) → 6,3',6'-tri-O-benzoylantirrhinoside + 6,2',6'-tri-O-benzoylantirrhinoside + 6,2',3',6'-tetra-O-benzoylantirrhinoside (202402-58-2)

Guidance literature:

With pyridine; In dichloromethane; at 4 ℃;

DOI:10.1002/(SICI)1099-0690(199802)1998:2<365::AID-EJOC365>3.0.CO;2-Z

Reference yield:

6,2',3',6'-tetra-O-benzoylantirrhinoside (202402-58-2) → Benzoic acid (1S,2S,3S,4S,5R)-4-formyloxymethyl-3-hydroxy-5-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) ozone; 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 15 min; 2.) CH₂Cl₂, MeOH, EtOH, -78 deg C, 1 h, RT, 1 h

2: 95 percent / NaIO₄ / acetone; H₂O / 1 h / 55 °C

3: NaCNBH₃, boric acid / methanol / 0 deg C, 45 min, 0 deg C to 20 deg C, 45 min

With sodium tetrahydroborate; sodium periodate; boric acid; sodium cyanoborohydride; ozone; In methanol; water; acetone;

DOI:10.1002/(SICI)1099-0690(199802)1998:2<365::AID-EJOC365>3.0.CO;2-Z

Reference yield:

6,2',3',6'-tetra-O-benzoylantirrhinoside (202402-58-2) → Benzoic acid (1S,2S,3R,4S,5R)-4-formyloxymethyl-3-hydroxy-5-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) ozone; 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 15 min; 2.) CH₂Cl₂, MeOH, EtOH, -78 deg C, 1 h, RT, 1 h

2: 95 percent / NaIO₄ / acetone; H₂O / 1 h / 55 °C

3: NaCNBH₃, boric acid / methanol / 0 deg C, 45 min, 0 deg C to 20 deg C, 45 min

With sodium tetrahydroborate; sodium periodate; boric acid; sodium cyanoborohydride; ozone; In methanol; water; acetone;

DOI:10.1002/(SICI)1099-0690(199802)1998:2<365::AID-EJOC365>3.0.CO;2-Z

upstream raw materials:

benzoyl chloride

anthirrinoside

Refernces