3,4,6-Tri-O-benzyl-D-glucofuranose

Base Information

• Chemical Name: 3,4,6-Tri-O-benzyl-D-glucofuranose
• CAS No.: 35958-64-6
• Molecular Formula: C₂₇H₃₀O₆
• Molecular Weight: 450.532
• European Community (EC) Number: 700-731-1
• DSSTox Substance ID: DTXSID001260651
• Nikkaji Number: J1.141.444C
• Mol file: 35958-64-6.mol

Synonyms:35958-64-6;3,4,6-Tri-O-benzyl-D-glucofuranose;DTXSID001260651;3-O,5-O,6-O-Tribenzyl-D-glucofuranose;3,5,6-Tris-O-(phenylmethyl)-D-glucofuranose;TBG (3R,4R,5R)-4-Benzyloxy-5-(1.2dibenzyloxyethil)tetrahydrofurane-2.3;(3R,4R,5R)-4-Benzyloxy-5-[(1R)-I,2-dibenzyloxyethyl] tetrahydrofuran-2,3-diol;(3R,4R,5R)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-4-phenylmethoxyoxolane-2,3-diol

Chemical Property of 3,4,6-Tri-O-benzyl-D-glucofuranose

Chemical Property:

• Boiling Point: 610.9±55.0 °C(Predicted)
• Density: 1.25±0.1 g/cm3(Predicted)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 450.20423867
• Heavy Atom Count: 33
• Complexity: 527

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC(C2C(C(C(O2)O)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@H]([C@@H]2[C@@H]([C@H](C(O2)O)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of 3,4,6-Tri-O-benzyl-D-glucofuranose

There total 13 articles about 3,4,6-Tri-O-benzyl-D-glucofuranose 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: 95.0%

1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside (53928-30-6) → 3,5,6-Tri-O-benzyl-α,β-D-glucofuranose (35958-64-6,81969-62-2,81969-65-5,114180-97-1,114180-98-2)

Guidance literature:

With acetic acid; for 4h; Heating;

Reference yield: 82.0%

1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside (53928-30-6) → 3,5,6-Tri-O-benzyl-D-glucofuranose (35958-64-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; at 0 - 20 ℃; for 6h;

DOI:10.1021/jacs.6b06937

Reference yield: 64.0%

C30H34O6 → 3,5,6-Tri-O-benzyl-D-glucofuranose (35958-64-6,81969-62-2,81969-65-5,114180-97-1,114180-98-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 0.666667h;

upstream raw materials:

methanol

1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

Downstream raw materials:

1,2-Di-O-acetyl-3,5,6-tri-O-benzyl-α,β-D-glucofuranose

3,5,6-Tris-O-benzyl-D-sorbitol

1,4-anhydro-3,5,6-tri-O-benzyl-D-fructose

1,4-anhydro-3,5,6-tri-O-benzyl-D-tagatose