methyl 2-O-allyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 2-O-allyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS No.: 767340-68-1
• Molecular Formula: C₃₃H₄₂O₆Si
• Molecular Weight: 562.778
• Mol file: 767340-68-1.mol

Synonyms:methyl 2-O-allyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property of methyl 2-O-allyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-allyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

There total 7 articles about methyl 2-O-allyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 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: 80.0%

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (20672-67-7) + Allylchlorodimethylsilane (4028-23-3) → methyl 2-O-allyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside (767340-68-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1021/jo049061w

Reference yield: 79.0%

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (20672-67-7) + allyldimethylsilyl triflate (150443-41-7) → methyl 2-O-allyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside (767340-68-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1021/jo049061w

Reference yield:

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) → methyl 2-O-allyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside (767340-68-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: K₂CO₃ / methanol / 2 h / 20 °C

2.1: NaH / dimethylformamide / 1 h / 0 °C

2.2: dimethylformamide / 24 h / 20 °C

3.1: 100 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 0 °C

4.1: 100 percent / K₂CO₃ / methanol / 1 h / 20 °C

5.1: 80 percent / imidazole / dimethylformamide / 24 h / 20 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; potassium carbonate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo049061w

upstream raw materials:

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside

Allylchlorodimethylsilane

allyldimethylsilyl triflate

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

Downstream raw materials:

1-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)prop-2-ene

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside

methyl 2-O-tert-butyl(dimethyl)silanyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

(1'E)-methyl 3,4,6-tri-O-benzyl-2-O-[dimethyl-(3'-trimethylsilanyl)prop-1'-enyl]silanyl-α-D-mannopyranoside