O-(1R,3R,4R)-3-(benzyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutyl O-p-tolyl carbonothioate

Base Information

Chemical Name:O-(1R,3R,4R)-3-(benzyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutyl O-p-tolyl carbonothioate
CAS No.:895532-59-9
Molecular Formula:C₂₅H₃₂O₅S
Molecular Weight:444.592
Hs Code.:

Synonyms:O-(1R,3R,4R)-3-(benzyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutyl O-p-tolyl carbonothioate

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Chemical Property of O-(1R,3R,4R)-3-(benzyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutyl O-p-tolyl carbonothioate

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Technology Process of O-(1R,3R,4R)-3-(benzyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutyl O-p-tolyl carbonothioate

There total 6 articles about O-(1R,3R,4R)-3-(benzyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutyl O-p-tolyl carbonothioate 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: 71.6%

: 895532-58-8
(1R,3R,4S)-3-benzyloxy-4-[2-(methoxymethoxy)ethyl]-2,2-dimethylcyclobutan-1-ol

: 937-63-3
p-Tolyl chlorothionoformate

: 895532-59-9
O-(1R,3R,4R)-3-(benzyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutyl O-p-tolyl carbonothioate

: S-(1R,3R,4R)-3-(benzyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutyl O-p-tolyl carbonothioate

Guidance literature:: With pyridine; dmap; In dichloromethane; for 48h;
DOI:10.1021/ol060827j

Reference yield:

: 895532-54-4
(1R,3R,4S)-3-benzyloxy-2,2-dimethyl-4-vinylcyclobutanol

: 895532-59-9
O-(1R,3R,4R)-3-(benzyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutyl O-p-tolyl carbonothioate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 °C

2.1: BH₃*THF / tetrahydrofuran / 4 h / -10 - 20 °C

2.2: 91 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 4 h / 0 - 20 °C

3.1: 100 percent / ethyldiisopropylamine / CHCl₃ / 48 h / 40 °C

4.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h

5.1: 71.6 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h

With pyridine; 2,6-dimethylpyridine; dmap; borane-THF; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1021/jo070861r

Reference yield:

: 895532-55-5
(1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-vinylcyclobutane

: 895532-59-9
O-(1R,3R,4R)-3-(benzyloxy)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutyl O-p-tolyl carbonothioate

Guidance literature:: Multi-step reaction with 4 steps

1.1: BH₃*THF / tetrahydrofuran / 4 h / -10 - 20 °C

1.2: 91 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 4 h / 0 - 20 °C

2.1: 100 percent / ethyldiisopropylamine / CHCl₃ / 48 h / 40 °C

3.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h

4.1: 71.6 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h

With pyridine; dmap; borane-THF; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1021/jo070861r