beta-D-Glucopyranoside, 4-((acetyloxy)methyl)phenyl, tetraacetate

Base Information

• Chemical Name: beta-D-Glucopyranoside, 4-((acetyloxy)methyl)phenyl, tetraacetate
• CAS No.: 59252-47-0
• Molecular Formula: C23H28 O12
• Molecular Weight: 496.468
• UNII: XQA4GK13X2
• Mol file: 59252-47-0.mol

Synonyms:ACETYLGASTRODIN [WHO-DD];.BETA.-D-GLUCOPYRANOSIDE, 4-((ACETYLOXY)METHYL)PHENYL, TETRAACETATE;.BETA.-D-GLUCOPYRANOSIDE, 4-((ACETYLOXY)METHYL)PHENYL, 2,3,4,6-TETRAACETATE

Chemical Property of beta-D-Glucopyranoside, 4-((acetyloxy)methyl)phenyl, tetraacetate

Chemical Property:

• Vapor Pressure: 1.31E-13mmHg at 25°C
• Boiling Point: 565.1°C at 760 mmHg
• Flash Point: 183.6°C
• PSA: 160.96000
• Density: 1.34g/cm³
• LogP: 0.65180
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 14
• Exact Mass: 496.15807632
• Heavy Atom Count: 35
• Complexity: 773

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC2=CC=C(C=C2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of beta-D-Glucopyranoside, 4-((acetyloxy)methyl)phenyl, tetraacetate

There total 11 articles about beta-D-Glucopyranoside, 4-((acetyloxy)methyl)phenyl, tetraacetate 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%

acetic anhydride (108-24-7) + (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (64291-41-4,105054-56-6) → 4-(tetra-O-acetyl-β-D-glucopyranosyloxy)benzyl acetate (59252-47-0)

Guidance literature:

With pyridine; at 100 ℃; for 6h;

DOI:10.1016/j.tetlet.2015.09.154

Reference yield:

acetic anhydride (108-24-7) + 3,4-Dimethoxy-benzoic acid 4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl ester → 4-(tetra-O-acetyl-β-D-glucopyranosyloxy)benzyl acetate (59252-47-0) + Veratric acid (93-07-2)

Guidance literature:

With pyridine; potassium hydroxide; Multistep reaction; 1.) methanol, r.t., 2.) r.t.;

Reference yield:

4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2887-07-2,31873-42-4,148579-45-7) → 4-(tetra-O-acetyl-β-D-glucopyranosyloxy)benzyl acetate (59252-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / methanol / 2 h / 20 °C

2: pyridine / 6 h / 100 °C

With pyridine; hydrogen; In methanol;

DOI:10.1016/j.tetlet.2015.09.154

upstream raw materials:

gastrodin

acetic anhydride

4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

4-hydroxy-benzaldehyde

Downstream raw materials:

4-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

gastrodin