phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside
• CAS No.: 152983-23-8
• Molecular Formula: C₂₃H₂₄O₇S
• Molecular Weight: 444.505
• Mol file: 152983-23-8.mol

Synonyms:phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside

There total 14 articles about phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside 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: 100.0%

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71676-30-7,87508-18-7,138922-03-9,87508-17-6) + acetic anhydride (108-24-7) → phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside (152983-23-8)

Guidance literature:

With pyridine;

Reference yield: 99.0%

benzaldehyde dimethyl acetal (1125-88-8) + phenyl 2,3-di-O-acetyl-1-thio-β-D-glucopyranoside (257614-58-7) → phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside (152983-23-8)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; In acetonitrile; at 60 ℃; for 0.166667h; regioselective reaction; Sonication; Inert atmosphere;

DOI:10.1039/c2ob25452b

Reference yield: 92.0%

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71676-30-7,87508-18-7,138922-03-9,87508-17-6) + acetyl chloride (75-36-5) → phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside (152983-23-8)

Guidance literature:

With aluminum oxide; In acetonitrile; at 20 ℃; for 0.666667h;

DOI:10.1016/j.carres.2005.11.035

upstream raw materials:

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

acetic anhydride

acetyl chloride

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

Downstream raw materials:

2,3-Di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl phenyl sulfone

phenyl 2,3-di-O-acetyl-6-O-benzyl-1-thio-β-D-glucopyranoside

phenyl 2,3-di-O-acetyl-1-thio-β-D-glucopyranoside

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol