(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentan-5-ol

Base Information

Chemical Name:(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentan-5-ol
CAS No.:646030-60-6
Molecular Formula:C₃₂H₄₈O₅Si
Molecular Weight:540.816
Hs Code.:

Synonyms:(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentan-5-ol

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Chemical Property of (2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentan-5-ol

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Technology Process of (2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentan-5-ol

There total 10 articles about (2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentan-5-ol 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: 87.0%

: 646030-59-3
(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-5-(tert-butyldimethylsilanyloxy)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentane

: 646030-60-6
(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentan-5-ol

Guidance literature:: With toluene-4-sulfonic acid; In methanol;
DOI:10.1021/ja038216z

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 646030-60-6
(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentan-5-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / KHMDS / tetrahydrofuran / 20 °C

2: 87 percent / aq. p-TsOH / methanol

With potassium hexamethylsilazane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol;
DOI:10.1021/ja038216z

Reference yield:

: 501015-46-9
(2R,3S)-(-)-3-methoxymethoxy-2,4-dimethylpent-4-en-1-ol

: 646030-60-6
(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentan-5-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 95.5 percent / imidazole / dimethylformamide / 3 h / 20 °C

2.1: ozone / CH₂Cl₂ / 1 h / -78 °C

2.2: 86 percent / PPh₃ / CH₂Cl₂ / 0.75 h / -78 °C

3.1: 93 percent / Et₃N / diethyl ether / 3 h / 20 °C

4.1: SnCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

5.1: 70 percent / LiI; LiAlH₄ / diethyl ether / 5 h / -100 °C

6.1: 82 percent / KHMDS / tetrahydrofuran / 20 °C

7.1: 87 percent / aq. p-TsOH / methanol

With 1H-imidazole; lithium aluminium tetrahydride; tin(IV) chloride; potassium hexamethylsilazane; toluene-4-sulfonic acid; ozone; triethylamine; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja038216z