phenyl 6-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 6-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
• CAS No.: 848568-09-2
• Molecular Formula: C₂₂H₂₄O₆S
• Molecular Weight: 416.495
• Mol file: 848568-09-2.mol

Synonyms:phenyl 6-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 6-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 6-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

There total 1 articles about phenyl 6-O-benzoyl-3,4-O-isopropylidene-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: 88.0%

benzoyl cyanide (613-90-1) + phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (120095-47-8) → phenyl 6-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (848568-09-2)

Guidance literature:

With triethylamine; In acetonitrile; at -40 ℃; for 5h;

DOI:10.1016/j.tetasy.2004.11.066

Reference yield: 80.0%

phenyl 6-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (848568-09-2) + levulinic acid (123-76-2) → phenyl 6-O-benzoyl-3,4-O-isopropylidene-2-O-levulinoyl-1-thio-β-D-galactopyranoside (848568-10-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at -20 - 20 ℃;

DOI:10.1016/j.tetasy.2004.11.066

Reference yield:

phenyl 6-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (848568-09-2) → Benzoic acid (2R,3R,4S,5R,6S)-3,4-dihydroxy-5-(4-oxo-pentanoyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / -20 - 20 °C

2: trifluoroacetic acid; water / CH₂Cl₂ / 1 h

With dmap; water; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.tetasy.2004.11.066

upstream raw materials:

benzoyl cyanide

phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

Downstream raw materials:

phenyl 6-O-benzoyl-3,4-O-isopropylidene-2-O-levulinoyl-1-thio-β-D-galactopyranoside

phenyl 3,4-di-O-acetyl-6-O-benzoyl-2-O-levulinoyl-1-thio-β-D-galactopyranoside