Scoloposide A

Base Information

• Chemical Name: Scoloposide A
• CAS No.: 21056-50-8
• Molecular Formula: C14H18O7
• Molecular Weight: 298.293
• Mol file: 21056-50-8.mol

Synonyms:Methyl6-O-benzoyl-b-D-glucopyranoside;methyl-(O6-benzoyl-β-D-glucopyranoside);Methyl-6-O-benzoyl-β-D-glucopyranosid;methyl 6-O-benzoyl-β-D-glucopyranoside;Methyl-(O6-benzoyl-β-D-glucopyranosid);Benzoic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester;

Chemical Property of Scoloposide A

Chemical Property:

• PSA: 105.45000
• LogP: -0.70260

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Scoloposide A

There total 10 articles about Scoloposide A 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: 99.0%

benzoyl chloride (98-88-4) + methyl beta-D-glucopyranoside (709-50-2) + methyl beta-D-galactopyranoside (1824-94-8) → methyl O3-benzoyl-β-D-galactoside (71454-34-7) + methyl O6-benzoyl-β-D-glucoside (21056-50-8)

Guidance literature:

methyl beta-D-glucopyranoside; methyl beta-D-galactopyranoside; With dibutyltin chloride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

benzoyl chloride; With 1,2,2,6,6-pentamethylpiperidine; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; chemoselective reaction;

DOI:10.1021/jo3024279

Reference yield: 99.0%

benzoyl chloride (98-88-4) + methyl beta-D-glucopyranoside (709-50-2) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl O6-benzoyl-β-D-glucoside (21056-50-8) + methyl O2-benzoyl-α-D-glucoside (21056-53-1)

Guidance literature:

methyl beta-D-glucopyranoside; methyl-alpha-D-glucopyranoside; With dibutyltin chloride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

benzoyl chloride; With 1,2,2,6,6-pentamethylpiperidine; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; chemoselective reaction;

DOI:10.1021/jo3024279

Reference yield: 79.0%

benzoyl chloride (98-88-4) + methyl beta-D-glucopyranoside (709-50-2) → methyl O6-benzoyl-β-D-glucoside (21056-50-8)

Guidance literature:

With dimethyltin dichloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 2.5h; regioselective reaction;

DOI:10.1021/ol802095e

upstream raw materials:

methyl 2,3,4-tri-O-benzoyl-6-O-acetyl-β-D-glucopyranoside

benzene

benzoyl chloride

methyl beta-D-glucopyranoside

Downstream raw materials:

methyl 2,3,4-tri-O-acetyl-6-O-benzoyl-β-D-glucopyranoside

Refernces

• 1、 Li, Yuyang,Kluger, Ronald. "Lead-Catalyzed Aqueous Benzoylation of Carbohydrates with an Acyl Phosphate Ester". . p. 7360 - 7365. Retrieved 2018/07/29.
• 2、 Muramatsu, Wataru,Takemoto, Yuki. "Selectivity switch in the catalytic functionalization of nonprotected carbohydrates: Selective synthesis in the presence of anomeric and structurally similar carbohydrates under mild conditions". . p. 2336 - 2345. Retrieved 2013/05/08.