1-(4-Chloro-phenyl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone

Base Information

• Chemical Name: 1-(4-Chloro-phenyl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone
• CAS No.: 110519-44-3
• Molecular Formula: C₄₂H₄₁ClO₆
• Molecular Weight: 677.237

Synonyms:1-(4-Chloro-phenyl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone

Chemical Property of 1-(4-Chloro-phenyl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone

Chemical Property:

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Technology Process of 1-(4-Chloro-phenyl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone

There total 2 articles about 1-(4-Chloro-phenyl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone 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: 83.0%

N-(1-(4-chlorophenyl)vinyl)piperidine (53927-05-2) + tetra-O-benzyl glucopyranosyl chloride (25320-59-6) → 1-(4-Chloro-phenyl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone (110519-44-3)

Guidance literature:

With 3 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 0.166667h; Ambient temperature; in the dark;

DOI:10.1039/c39880000057

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane (58518-76-6) → 1-(4-Chloro-phenyl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone (110519-44-3)

Guidance literature:

With boron trifluoride diethyl etherate; trifluoroacetic anhydride; Yield given. Multistep reaction; 1.) dichloromethane, 30 min; 2.) dichloromethane, 15 min;

DOI:10.1039/c39870001245

Reference yield: 87.0%

1-(4-Chloro-phenyl)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethanone (110519-44-3) → 1-(4-chlorophenyl)-2-(2′,3,4′,6′-tetra-O-benzyl-β-D-glycopyranosyl)ethanone (124813-91-8)

Guidance literature:

With potassium carbonate; In methanol; for 20h; Ambient temperature; KOH, 0.8 h;

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane

N-(1-(4-chlorophenyl)vinyl)piperidine

tetra-O-benzyl glucopyranosyl chloride

Downstream raw materials:

1-(4-chlorophenyl)-2-(2′,3,4′,6′-tetra-O-benzyl-β-D-glycopyranosyl)ethanone

2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol

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