1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose

Base Information

• Chemical Name: 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose
• CAS No.: 39686-94-7
• Molecular Formula: C₂₁H₂₆O₁₀
• Molecular Weight: 438.431
• DSSTox Substance ID: DTXSID50455622
• Nikkaji Number: J1.799.464F
• Wikidata: Q72497751
• Mol file: 39686-94-7.mol

Synonyms:39686-94-7;1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose;1,2,4,6-Tetra-O-acetyl-3-O-benzyl-b-D-glucopyranose;[(2R,3R,4S,5R,6S)-3,5,6-triacetyloxy-4-phenylmethoxyoxan-2-yl]methyl acetate;(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)-4-(benzyloxy)tetrahydro-2H-pyran-2,3,5-triyl triacetate;SCHEMBL971366;DTXSID50455622;SJPSXDYBIIGRQJ-YMQHIKHWSA-N;AMY41543;BS-28044;W-202630;1-O,2-O,4-O,6-O-Tetraacetyl-3-O-benzyl-beta-D-glucopyranose;(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)-4-(benzyloxy)tetrahydro-2H-pyran-2,3,5-triyltriacetate

Chemical Property of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose

Chemical Property:

• Melting Point: 107℃
• Boiling Point: 514.2±50.0 °C(Predicted)
• PSA: 123.66000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 1.28630
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 438.15259702
• Heavy Atom Count: 31
• Complexity: 642

Purity/Quality:

97% ^*data from raw suppliers

1-2-4-6-Tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose ^*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)OC(=O)C)OC(=O)C)OCC2=CC=CC=C2)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)C)OC(=O)C)OCC2=CC=CC=C2)OC(=O)C

Technology Process of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose

There total 29 articles about 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose 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%

3-O-benzyl-D-glucopyranose (65877-63-6,97590-76-6,99396-09-5,5531-09-9) + acetic anhydride (108-24-7) → 3-O-benzyl-1,2,4,6-tetra-O-acetyl-D-glucopyranose (39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9)

Guidance literature:

With pyridine; at 20 ℃; for 8h;

DOI:10.1016/j.tet.2018.03.057

Reference yield: 86.0%

acetic anhydride (108-24-7) + 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose (591727-19-4) → 3-O-benzyl-1,2,4,6-tetra-O-acetyl-D-glucopyranose (39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9)

Guidance literature:

1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose; With hydrogenchloride; In water; at 80 ℃; for 2h;

acetic anhydride; With sodium acetate; at 80 ℃; for 4h;

Reference yield: 85.0%

3-O-benzyl-D-glucopyranose (65877-63-6,97590-76-6,99396-09-5,5531-09-9) + acetic anhydride (108-24-7) → 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9)

Guidance literature:

With pyridine; at 20 ℃; for 15h;

DOI:10.1021/ol300669v

upstream raw materials:

O³-benzyl-D-glucose

acetic anhydride

3-O-benzyl-D-glucopyranose

benzyl-O-β-D-glucopyranoside

Downstream raw materials:

methyl β-D-glucopyranoside 3-benzyl ether

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

methyl 3-O-benzyl-6-O-trityl-β-D-glucopyranoside

methyl 3-O-benzyl-2,4-di-O-(trifluoromethanesulfonyl)-6-O-trityl-β-D-glucopyranoside