Benzyl 2-O,3-O,4-O,6-O-tetrabenzyl-beta-D-glucopyranoside

Base Information

• Chemical Name: Benzyl 2-O,3-O,4-O,6-O-tetrabenzyl-beta-D-glucopyranoside
• CAS No.: 67890-29-3
• Molecular Formula: C₄₁H₄₂O₆
• Molecular Weight: 630.781
• DSSTox Substance ID: DTXSID701166713
• Nikkaji Number: J2.349.209A
• Mol file: 67890-29-3.mol

Synonyms:DTXSID701166713;Benzyl 2-O,3-O,4-O,6-O-tetrabenzyl-beta-D-glucopyranoside;Phenylmethyl 2,3,4,6-tetrakis-O-(phenylmethyl)-beta-D-glucopyranoside;67890-29-3

Chemical Property of Benzyl 2-O,3-O,4-O,6-O-tetrabenzyl-beta-D-glucopyranoside

Chemical Property:

• XLogP3: 7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 16
• Exact Mass: 630.29813906
• Heavy Atom Count: 47
• Complexity: 809

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C(C(O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6

Technology Process of Benzyl 2-O,3-O,4-O,6-O-tetrabenzyl-beta-D-glucopyranoside

There total 51 articles about Benzyl 2-O,3-O,4-O,6-O-tetrabenzyl-beta-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: 96.0%

(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran (194088-19-2) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2,3,4,6-tetra-O-benzyl-β-D-gluco-pyranoside (67890-29-3)

Guidance literature:

With FeCl₃/C; In acetonitrile; at 60 ℃; for 3h; Reagent/catalyst; Temperature; stereoselective reaction; Mechanism; Inert atmosphere; Green chemistry;

DOI:10.1055/s-0037-1611801

Reference yield: 95.0%

benzyl alcohol (100-51-6,185532-71-2) + 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranosyl N-trichloroacetylcarbamate → benzyl 2,3,4,6-tetra-O-benzyl-β,α-D-glucopyranoside (4132-31-4,67890-29-3,89615-39-4,89615-40-7,89615-41-8,61277-57-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.1h;

DOI:10.1016/j.carres.2005.07.024

Reference yield: 92.0%

propargyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (4132-31-4,61277-57-4,67890-29-3,89615-39-4,89615-40-7,89615-41-8)

Guidance literature:

With FeCl₃/C; In acetonitrile; at 60 ℃; for 5h; stereoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1055/s-0037-1611801

upstream raw materials:

benzyl chloride

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

1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

benzyl alcohol

Downstream raw materials:

benzyl 2,3,4-tri-O-benzyl-D-glucopyranoside

benzyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 6-(hydrogen succinate)

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

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside