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

Base Information

• Chemical Name: 1-(4-chlorophenyl)-2-(2′,3,4′,6′-tetra-O-benzyl-β-D-glycopyranosyl)ethanone
• CAS No.: 124813-91-8
• Molecular Formula: C₄₂H₄₁ClO₆
• Molecular Weight: 677.237

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

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

Chemical Property:

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

There total 7 articles about 1-(4-chlorophenyl)-2-(2′,3,4′,6′-tetra-O-benzyl-β-D-glycopyranosyl)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: 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;

Reference yield: 75.0%

1-N-methoxy-N-methyl-2-(2′,3′,4′,6′-tetra-O-benzyl-β-D-glycopyranosyl)acetamide + (4-chlorphenyl)magnesium bromide (873-77-8) → 1-(4-chlorophenyl)-2-(2′,3,4′,6′-tetra-O-benzyl-β-D-glycopyranosyl)ethanone (124813-91-8)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/ejoc.201701468

Reference yield:

3,5-bis(trifluoromethyl)benzenesulfonyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside + para-chloroacetophenone (99-91-2) → C42H41ClO6 + 1-(4-chlorophenyl)-2-(2′,3,4′,6′-tetra-O-benzyl-β-D-glycopyranosyl)ethanone (124813-91-8)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - -30 ℃; for 1h;

DOI:10.1002/anie.201914221

upstream raw materials:

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

(4-chlorphenyl)magnesium bromide

((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

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

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