(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

Base Information

Chemical Name:(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
CAS No.:646030-59-3
Molecular Formula:C₃₈H₆₂O₅Si₂
Molecular Weight:655.078
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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: 82.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 646030-54-8
(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-5-(tert-butyldimethylsilanyloxy)-3-methoxymethoxy-4-methylpentan-2-ol

: 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

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ja038216z

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 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

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 6 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

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