2,3,6-tri-O-benzyl-4-deoxy-4-C-(2,2-dibromoethenyl)-D-glucono-1,5-lactone

Base Information

• Chemical Name: 2,3,6-tri-O-benzyl-4-deoxy-4-C-(2,2-dibromoethenyl)-D-glucono-1,5-lactone
• CAS No.: 167646-36-8
• Molecular Formula: C₂₉H₂₈Br₂O₅
• Molecular Weight: 616.346

Synonyms:2,3,6-tri-O-benzyl-4-deoxy-4-C-(2,2-dibromoethenyl)-D-glucono-1,5-lactone

Chemical Property of 2,3,6-tri-O-benzyl-4-deoxy-4-C-(2,2-dibromoethenyl)-D-glucono-1,5-lactone

Chemical Property:

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Technology Process of 2,3,6-tri-O-benzyl-4-deoxy-4-C-(2,2-dibromoethenyl)-D-glucono-1,5-lactone

There total 1 articles about 2,3,6-tri-O-benzyl-4-deoxy-4-C-(2,2-dibromoethenyl)-D-glucono-1,5-lactone 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:

2,3,6-tri-O-benzyl-4-deoxy-4-C-(2,2-dibromoethenyl)-D-glucopyranoside → 2,3,6-tri-O-benzyl-4-deoxy-4-C-(2,2-dibromoethenyl)-D-glucono-1,5-lactone (167646-36-8)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; Yield given; -65 deg C, 20 min.; -40 deg C, 20 min.;

DOI:10.1002/hlca.19950780122

Reference yield: 90.0%

lithium trimethylsilylacetylenide (54655-07-1) + 2,3,6-tri-O-benzyl-4-deoxy-4-C-(2,2-dibromoethenyl)-D-glucono-1,5-lactone (167646-36-8) → 4,5,8-tri-O-benzyl-6-C-(2,2-dibromoethenyl)-1,1,2,2-tetradehydro-1,2,6-trideoxy-1-C-(trimethylsilyl)-D-gluco-oct-3-ulopyranose

Guidance literature:

With cerium(III) chloride; In tetrahydrofuran; hexane; at -76 - -45 ℃; for 1.5h;

DOI:10.1002/hlca.19950780122

Reference yield:

1-<<3--3-methylbutoxy>methyl>-4-methoxybenzene (170474-54-1) + 2,3,6-tri-O-benzyl-4-deoxy-4-C-(2,2-dibromoethenyl)-D-glucono-1,5-lactone (167646-36-8) → 4,5,8-tri-O-benzyl-1,1,2,2-tetradehydro-1,2,6-trideoxy-6-C-(2,2-dibromoethenyl)-1-C-<<1,1-dimethyl-3-(4-methoxybenzyloxy)propyl>dimethylsilyl>-α-D-gluco-oct-3-ulopyranose + 4,5,8-tri-O-benzyl-1,1,2,2-tetradehydro-1,2,6-trideoxy-6-C-(2,2-dibromoethenyl)-1-C-<<1,1-dimethyl-3-(4-methoxybenzyloxy)propyl>dimethylsilyl>-β-D-gluco-oct-3-ulopyranose

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, hexane, -76 degC, 20 min, -76 to -15 degC, 10 min, -15 degC, 10 min; 2.) -76 degC, 0.5 h;

DOI:10.1002/hlca.19950780319

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