phenyl 2,3-di-O-acetyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,3-di-O-acetyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside
• CAS No.: 1248348-95-9
• Molecular Formula: C₂₄H₂₆O₈S
• Molecular Weight: 474.532
• Mol file: 1248348-95-9.mol

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

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

There total 7 articles about phenyl 2,3-di-O-acetyl-4,6-O-(4-methoxybenzylidene)-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: 99.0%

acetic anhydride (108-24-7) + phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside (273749-60-3) → phenyl 2,3-di-O-acetyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside (1248348-95-9)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201701238

Reference yield:

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → phenyl 2,3-di-O-acetyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside (1248348-95-9)

Guidance literature:

Multi-step reaction with 4 steps

1: boron trifluoride diethyl etherate / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

2: ammonium hydroxide / methanol / 19 h / Inert atmosphere; Schlenk technique

3: toluene-4-sulfonic acid / acetonitrile / 4 h / 40 °C / Inert atmosphere; Schlenk technique

4: dmap / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique

With dmap; ammonium hydroxide; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetonitrile;

DOI:10.1002/chem.201701238

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → phenyl 2,3-di-O-acetyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside (1248348-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / acetonitrile / 2 h / 80 °C

2: pyridine / 2 h / 20 °C

With pyridine; toluene-4-sulfonic acid; In acetonitrile;

DOI:10.1016/j.tet.2012.06.081

upstream raw materials:

acetic anhydride

phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside

p-Anisaldehyde dimethyl acetal

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

methyl (2,3-di-O-acetyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->4)-2,6-di-O-benzyl-3-deoxy-3-C-(methyl sulfonatomethyl)-α-D-glucopyranoside