2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose

Base Information

• Chemical Name: 2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose
• CAS No.: 99571-46-7
• Molecular Formula: C₃₃H₃₆O₁₀
• Molecular Weight: 592.643
• Mol file: 99571-46-7.mol

Synonyms:2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose

Chemical Property of 2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose

There total 8 articles about 2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose 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: 89.0%

O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-26-6,99571-45-6) → 1,6-anhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-glucopyranose (97390-28-8,99571-46-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In various solvent(s); for 3h; Ambient temperature;

DOI:10.1016/0008-6215(85)85222-8

Reference yield:

1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-18-6) → 1,6-anhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-glucopyranose (97390-28-8,99571-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 6 percent / 2,4,6-collidine / CH₂Cl₂ / -60 °C

2: 89 percent / tetrabutylammonium fluoride / various solvent(s) / 3 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; tetrabutyl ammonium fluoride; In dichloromethane;

DOI:10.1016/0008-6215(85)85222-8

Reference yield:

2I,II,3I,II-tetra-O-acetyl-4II,6II-O-benzylidene-1I,6Ianhydro-β-cellobiose (97415-74-2) → 1,6-anhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-glucopyranose (97390-28-8,99571-46-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / sodium methoxide / methanol / 10 h / Ambient temperature

2: 1.) pyridine; 2.) pyridine / 1.) r.t., 10 h; 2.) r.t., 6 h

3: 94 percent / hydrazine monohydrate / methanol; various solvent(s) / 10 h / Ambient temperature

4: 6 percent / 2,4,6-collidine / CH₂Cl₂ / -60 °C

5: 89 percent / tetrabutylammonium fluoride / various solvent(s) / 3 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; tetrabutyl ammonium fluoride; sodium methylate; hydrazine hydrate; In methanol; dichloromethane;

DOI:10.1016/0008-6215(85)85222-8

upstream raw materials:

O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

benzyl trifluoromethyl sulfone

benzyl bromide

1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

Downstream raw materials:

O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose

O-(methyl 2,3-di-O-benzyl-4-O-(chloroacetyl)-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose