2-Formylphenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside

Base Information

• Chemical Name: 2-Formylphenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside
• CAS No.: 14581-83-0
• Molecular Formula: C₂₁H₂₄O₁₁
• Molecular Weight: 452.415
• Hs Code.: 2938909090
• ChEMBL ID: CHEMBL559406
• DSSTox Substance ID: DTXSID80471274
• Nikkaji Number: J536.251B
• Wikidata: Q82299752
• Mol file: 14581-83-0.mol

Synonyms:14581-83-0;2-Formylphenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside;[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-formylphenoxy)oxan-2-yl]methyl acetate;Benzaldehyde, 2-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-;CHEMBL559406;SCHEMBL2338993;DTXSID80471274;W-201285;2'-Formylphenyl 2,3,4,6-tetra-o-acetyl-beta-d-glucopyranoside;2-Formylphenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside?;2/'-FORMYLPHENYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE

Chemical Property of 2-Formylphenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside

Chemical Property:

• PSA: 140.73000
• LogP: 0.96100
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 452.13186158
• Heavy Atom Count: 32
• Complexity: 706

Purity/Quality:

≥98% ^*data from raw suppliers

2-Formylphenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside ^*data from reagent 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=CC=C2C=O)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=CC=C2C=O)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2-Formylphenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside

There total 7 articles about 2-Formylphenyl 2,3,4,6-tetra-O-acetyl-b-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: 90.0%

acetic anhydride (108-24-7) + helicin (618-65-5) → helicin acetate (14581-83-0,142393-06-4,148615-67-2)

Guidance literature:

With pyridine; at 0 ℃; for 1.5h;

DOI:10.1139/v96-172

Reference yield: 88.0%

helicin + acetic anhydride (108-24-7) → helicin acetate (14581-83-0,142393-06-4,148615-67-2)

Guidance literature:

With pyridine; for 16h;

DOI:10.1021/jm070315q

Reference yield: 78.1%

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) + salicylaldehyde (90-02-8) → helicin acetate (14581-83-0,142393-06-4,148615-67-2)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; water; for 8h; Reflux;

DOI:10.1007/s10600-016-1721-5

upstream raw materials:

salicylaldehyde

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

β-D-glucose pentaacetate

acetic anhydride

Downstream raw materials:

isonicotinic acid-[2-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzylidenehydrazide]

2-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzaldehyde-(4-hydroxy-phenylimine)

2-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzaldehyde-(4-methoxy-phenylimine)

4-[2-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzylidenamino]-benzoic acid