(1R,2S,3S)-2-(benzyloxy)methyl-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-diol

Base Information

Chemical Name:(1R,2S,3S)-2-(benzyloxy)methyl-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-diol
CAS No.:1383003-84-6
Molecular Formula:C₁₉H₂₈O₃
Molecular Weight:304.43
Hs Code.:

Synonyms:(1R,2S,3S)-2-(benzyloxy)methyl-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-diol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2S,3S)-2-(benzyloxy)methyl-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-diol

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Technology Process of (1R,2S,3S)-2-(benzyloxy)methyl-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-diol

There total 4 articles about (1R,2S,3S)-2-(benzyloxy)methyl-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-diol 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: 40.0%

: 303142-74-7
(S)-2-((benzyloxy)methyl)-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-dione

: 1383003-84-6
(1R,2S,3S)-2-(benzyloxy)methyl-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-diol

Guidance literature:: With zinc(II) tetrahydroborate; In tetrahydrofuran; dichloromethane; at 0 - 40 ℃; for 17h; Inert atmosphere;
DOI:10.1021/ja3032345

Reference yield:

: 856177-89-4
2-((benzyloxy)methyl)-2-methylcyclopentane-1,3-dione

: 1383003-84-6
(1R,2S,3S)-2-(benzyloxy)methyl-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-diol

Guidance literature:: Multi-step reaction with 5 steps

1: copper(ll) bromide / methanol / 1 h / Inert atmosphere; Reflux

2: C₅₈H₅₈NO₂P; copper(II) bis(trifluoromethanesulfonate) / diethyl ether; hexane / 0.5 h / -78 - 20 °C / Inert atmosphere

3: diethyl ether; hexane / 0.5 h / -40 °C / Inert atmosphere

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / 20 - 80 °C / Inert atmosphere

5: zinc(II) tetrahydroborate / tetrahydrofuran; dichloromethane / 17 h / 0 - 40 °C / Inert atmosphere

With zinc(II) tetrahydroborate; C₅₈H₅₈NO₂P; copper(II) bis(trifluoromethanesulfonate); 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(ll) bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/ja3032345

Reference yield:

: 1383003-82-4
(2S,4R,5S)-2-(benzyloxy)methyl-4-((R)-1-hydroxybutyl)-2,5-dimethylcyclopentane-1,3-dione

: 1383003-84-6
(1R,2S,3S)-2-(benzyloxy)methyl-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / 20 - 80 °C / Inert atmosphere

2: zinc(II) tetrahydroborate / tetrahydrofuran; dichloromethane / 17 h / 0 - 40 °C / Inert atmosphere

With zinc(II) tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja3032345