2-O-Benzoyl-4.6-benzyliden-3-O-(tetrahydropyran-2-yl)-α-D-glucopyranose-methylether

Base Information

• Chemical Name: 2-O-Benzoyl-4.6-benzyliden-3-O-(tetrahydropyran-2-yl)-α-D-glucopyranose-methylether
• CAS No.: 50680-06-3
• Molecular Formula: C₂₆H₃₀O₈
• Molecular Weight: 470.519
• Mol file: 50680-06-3.mol

Synonyms:2-O-Benzoyl-4.6-benzyliden-3-O-(tetrahydropyran-2-yl)-α-D-glucopyranose-methylether

Chemical Property of 2-O-Benzoyl-4.6-benzyliden-3-O-(tetrahydropyran-2-yl)-α-D-glucopyranose-methylether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-Benzoyl-4.6-benzyliden-3-O-(tetrahydropyran-2-yl)-α-D-glucopyranose-methylether

There total 9 articles about 2-O-Benzoyl-4.6-benzyliden-3-O-(tetrahydropyran-2-yl)-α-D-glucopyranose-methylether 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%

3,4-dihydro-2H-pyran (110-87-2) + methyl 4,6-O-benzylidene-2-O-benzoyl-α-D-glucopyranoside (28642-64-0) → 2-O-Benzoyl-4.6-benzyliden-3-O-(tetrahydropyran-2-yl)-α-D-glucopyranose-methylether (50680-06-3)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2007.03.031

Reference yield:

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) → 2-O-Benzoyl-4.6-benzyliden-3-O-(tetrahydropyran-2-yl)-α-D-glucopyranose-methylether (50680-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / toluene; methanol / 14 h / 55 °C

1.2: Et₃N / dioxane / 4 h / 20 °C

2.1: 95 percent / P-TsOH / CH₂Cl₂ / 1 h / 20 °C

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; In methanol; dichloromethane; toluene;

DOI:10.1016/j.tetlet.2007.03.031

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-O-Benzoyl-4.6-benzyliden-3-O-(tetrahydropyran-2-yl)-α-D-glucopyranose-methylether (50680-06-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 79 percent / dimethylformamide / 1 h / 60 °C

2.1: Bu₂SnO / toluene; methanol / 14 h / 55 °C

2.2: Et₃N / dioxane / 4 h / 20 °C

3.1: 95 percent / P-TsOH / CH₂Cl₂ / 1 h / 20 °C

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2007.03.031

upstream raw materials:

3,4-dihydro-2H-pyran

methyl 4,6-O-benzylidene-2-O-benzoyl-α-D-glucopyranoside

methyl 4,6-O-benzylidene-α-D-glucopyranoside

benzaldehyde dimethyl acetal

Downstream raw materials:

4.6-O-Benzyliden-3-O-(tetrahydropyran-2-yl)-α-D-glucopyranose-methylether

methyl 3,4-di-O-benzyl-2-C-benzyloxymethyl-2-deoxy-α-D-glucopyranoside

methyl 3,4-di-O-benzyl-2-C-benzyloxymethyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

(3S,4R,5R,6S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-6-methoxy-2-methylene-tetrahydro-pyran