dimethyl 2-(benzyloxy)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate

Base Information

Chemical Name:dimethyl 2-(benzyloxy)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate
CAS No.:952716-31-3
Molecular Formula:C₁₈H₂₇O₆P
Molecular Weight:370.383
Hs Code.:

Synonyms:dimethyl 2-(benzyloxy)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate

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Chemical Property of dimethyl 2-(benzyloxy)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate

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Technology Process of dimethyl 2-(benzyloxy)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate

There total 6 articles about dimethyl 2-(benzyloxy)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate 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: 36.0%

: 952716-29-9
dimethyl 2-hydroxy-2-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate

: 100-39-0
benzyl bromide

: 952716-31-3
dimethyl 2-(benzyloxy)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate

Guidance literature:: With silver(l) oxide; In N,N-dimethyl-formamide; at 20 ℃; for 48h;
DOI:10.1016/j.tet.2007.07.032

Reference yield:

: 1058706-86-7
(S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane

: 952716-31-3
dimethyl 2-(benzyloxy)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: nBuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

1.2: tetrahydrofuran; hexane; CH₂Cl₂ / 0.25 h

2.1: 36 percent / Ag₂O / dimethylformamide / 48 h / 20 °C

With n-butyllithium; silver(l) oxide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2007.07.032

Reference yield:

: 108817-96-5
[(4S,5S)-5-[(tert-butyl(dimethyl)silyl)oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

: 952716-31-3
dimethyl 2-(benzyloxy)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylphosphonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / 0.25 h / -50 °C

2.1: 16.3 g / sodium hydride; dimethylsulfoxide / tetrahydrofuran; various solvent(s) / 20 °C

3.1: 83 percent / Bu₄NF / tetrahydrofuran

4.1: dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -50 - 20 °C

5.1: nBuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

5.2: tetrahydrofuran; hexane; CH₂Cl₂ / 0.25 h

6.1: 36 percent / Ag₂O / dimethylformamide / 48 h / 20 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; silver(l) oxide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation / 2.1: Wittig reaction / 4.1: Swern oxidation;
DOI:10.1016/j.tet.2007.07.032