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

Base Information

Chemical Name:(2R,3S,4S,2'R,4'S,5'S)-5-(5-allyl-4-methyltetrahydrofuran-2-yl)-4-(4-methoxybenzyloxy)-3-methoxymethoxy-4-methylpentan-1-ol
CAS No.:646030-55-9
Molecular Formula:C₂₄H₃₈O₆
Molecular Weight:422.562
Hs Code.:

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

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

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

There total 13 articles about (2R,3S,4S,2'R,4'S,5'S)-5-(5-allyl-4-methyltetrahydrofuran-2-yl)-4-(4-methoxybenzyloxy)-3-methoxymethoxy-4-methylpentan-1-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: 93.0%

: 646030-69-5
(2R,3S,4S,2'R,4'S,5'S)-(-)-[5-(5-allyl-4-methyltetrahydrofuran-2-yl)-4-(4-methoxybeznyloxy)-3-methoxymethoxy-4-methylpentyloxy]tert-butyldimethylsilane

: 646030-55-9
(2R,3S,4S,2'R,4'S,5'S)-5-(5-allyl-4-methyltetrahydrofuran-2-yl)-4-(4-methoxybenzyloxy)-3-methoxymethoxy-4-methylpentan-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1.5h;
DOI:10.1021/ja038216z

Reference yield:

: 501015-48-1
(3S,4R)-(-)-5-(tert-butyldimethylsilanyloxy)-3-methoxymethoxy-4-methylpentan-2-one

: 646030-55-9
(2R,3S,4S,2'R,4'S,5'S)-5-(5-allyl-4-methyltetrahydrofuran-2-yl)-4-(4-methoxybenzyloxy)-3-methoxymethoxy-4-methylpentan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / Et₃N / diethyl ether / 3 h / 20 °C

2: SnCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

3: 11 percent / LiI; LiAlH₄ / diethyl ether / 5 h / -100 °C

4: 77 percent / KHMDS / tetrahydrofuran; dimethylformamide / 16 h / 20 °C

5: 93 percent / TBAF / tetrahydrofuran / 1.5 h

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

Reference yield:

: 501015-44-7
(2'S,3'R,4S,5R)-(-)-3-(3-hydroxy-2,4-dimethylpent-4-enoyl)-4-methyl-5-phenyloxazolidin-2-one

: 646030-55-9
(2R,3S,4S,2'R,4'S,5'S)-5-(5-allyl-4-methyltetrahydrofuran-2-yl)-4-(4-methoxybenzyloxy)-3-methoxymethoxy-4-methylpentan-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / i-Pr₂NEt / CH₂Cl₂ / 23 h / 0 - 20 °C

2.1: 78 percent / LiBH₄; water / diethyl ether / 2 h

3.1: 95.5 percent / imidazole / dimethylformamide / 3 h / 20 °C

4.1: ozone / CH₂Cl₂ / 1 h / -78 °C

4.2: 86 percent / PPh₃ / CH₂Cl₂ / 0.75 h / -78 °C

5.1: 93 percent / Et₃N / diethyl ether / 3 h / 20 °C

6.1: SnCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

7.1: 11 percent / LiI; LiAlH₄ / diethyl ether / 5 h / -100 °C

8.1: 77 percent / KHMDS / tetrahydrofuran; dimethylformamide / 16 h / 20 °C

9.1: 93 percent / TBAF / tetrahydrofuran / 1.5 h

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