benzyl 6-deoxy-6-(diethylphosphonomethyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Base Information

Chemical Name:benzyl 6-deoxy-6-(diethylphosphonomethyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
CAS No.:291527-98-5
Molecular Formula:C₃₉H₄₇O₈P
Molecular Weight:674.771
Hs Code.:

Synonyms:benzyl 6-deoxy-6-(diethylphosphonomethyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

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Chemical Property of benzyl 6-deoxy-6-(diethylphosphonomethyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

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Technology Process of benzyl 6-deoxy-6-(diethylphosphonomethyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

There total 5 articles about benzyl 6-deoxy-6-(diethylphosphonomethyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 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: 74.0%

: 683-08-9
Diethyl methylphosphonate

: 151075-88-6
benzyl 2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside

: 291527-98-5
benzyl 6-deoxy-6-(diethylphosphonomethyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 0.166667h;
DOI:10.1021/jo000220v

Reference yield:

: 27851-29-2
benzyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 291527-98-5
benzyl 6-deoxy-6-(diethylphosphonomethyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1.5 h / -40 °C

2: 74 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.17 h / -78 °C

With n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; 1: sulfonylation / 2: Substitution;
DOI:10.1021/jo000220v

Reference yield:

: 291528-10-4
benzyl 6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside

: 291527-98-5
benzyl 6-deoxy-6-(diethylphosphonomethyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / NaH / dimethylformamide / 7 h / 20 °C

2: 88 percent / TBAF / tetrahydrofuran / 9 h / 20 °C

3: 99 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1.5 h / -40 °C

4: 74 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.17 h / -78 °C

With n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: desilylation / 3: sulfonylation / 4: Substitution;
DOI:10.1021/jo000220v