(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one

Base Information

Chemical Name:(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one
CAS No.:681853-94-1
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one

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Chemical Property of (+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one

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Technology Process of (+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one

There total 6 articles about (+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one 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: 92.0%

: 97204-83-6
(1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol

: 681853-94-1
(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/jo0356762

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 681853-94-1
(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: KO-tBu / tetrahydrofuran / 12 h / 20 °C

1.2: Bu₂SnO / toluene / Heating

1.3: 80 percent / TBAI / 16 h / 75 °C

2.1: (COCl)2; DMSO / CH₂Cl₂ / 1 h / -78 °C

2.2: 92 percent / Et₃N / 1 h / 20 °C

With oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1.1: Wittig reaction / 2.1: Swern oxidation;
DOI:10.1246/cl.2004.506

Reference yield:

: 100-39-0
benzyl bromide

: 681853-94-1
(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 80 percent / tetrabutylammonium iodide / toluene / 16 h / 75 °C

2.1: 92 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / 20 °C

With oxalyl dichloride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 2.1: Swern oxidation;
DOI:10.1021/jo0356762