(4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Base Information

Chemical Name:(4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde
CAS No.:495397-67-6
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:(4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

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Chemical Property of (4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Chemical Property:

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Technology Process of (4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

There total 16 articles about (4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 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:

: 848862-73-7
1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-keto-D-erythro-pentitol

: 495397-67-6
(4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

1.2: 92 percent / tetrahydrofuran; hexane / 16 h / 20 °C

2.1: 97 percent / tetrabutylammonium fluoride / acetonitrile / 2 h / 20 °C

3.1: 98 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -70 - 20 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 3.1: Swern oxidation;
DOI:10.1016/j.tetasy.2004.11.069

Reference yield:

: 117174-48-8
1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-D-ribitol

: 495397-67-6
(4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -70 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.2: 92 percent / tetrahydrofuran; hexane / 16 h / 20 °C

3.1: 97 percent / tetrabutylammonium fluoride / acetonitrile / 2 h / 20 °C

4.1: 98 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -70 - 20 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 1.1: Swern oxidation / 4.1: Swern oxidation;
DOI:10.1016/j.tetasy.2004.11.069

Reference yield:

: 848862-75-9
1-O-tert-butyldiphenylsilyl-5-O-benzyl-2,3-O-isopropylidene-4-C-methylene-D-erythro-pentitol

: 495397-67-6
(4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / tetrabutylammonium fluoride / acetonitrile / 2 h / 20 °C

2: 98 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -70 - 20 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In dichloromethane; acetonitrile; 2: Swern oxidation;
DOI:10.1016/j.tetasy.2004.11.069