methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-D-mannopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-D-mannopyranoside
• CAS No.: 95519-67-8
• Molecular Formula: C₂₁H₂₃FO₅
• Molecular Weight: 374.409

Synonyms:methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-D-mannopyranoside

Chemical Property of methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-D-mannopyranoside

Chemical Property:

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Technology Process of methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-D-mannopyranoside

There total 2 articles about methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-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: 77.0%

methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside (95587-91-0) → methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-D-mannopyranoside (95519-67-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In acetonitrile; for 0.5h; Heating;

DOI:10.1248/cpb.32.4758

Reference yield:

methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (129706-93-0) → methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-D-mannopyranoside (95519-67-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / pyridine / 2 h / 0 °C

2: 77 percent / tetrabutylammonium fluoride / acetonitrile / 0.5 h / Heating

With tetrabutyl ammonium fluoride; In pyridine; acetonitrile;

DOI:10.1248/cpb.32.4758

Reference yield: 88.0%

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-D-mannopyranoside (95519-67-8) → 2-deoxy-2-fluoro-D-mannopyranoside (7226-39-3,7241-17-0,28876-44-0,38711-37-4,55449-80-4,62182-10-9,62182-14-3,86783-82-6,98856-44-1,98856-45-2,98856-46-3,31077-88-0)

Guidance literature:

With methanesulfonic acid; water; for 0.333333h; Heating;

DOI:10.1248/cpb.32.4758

upstream raw materials:

methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside

methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Downstream raw materials:

2-deoxy-2-fluoro-D-mannopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranoside

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