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

Base Information

Chemical Name:(2S,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-5-iodopentane
CAS No.:501015-57-2
Molecular Formula:C₃₂H₄₇IO₄Si
Molecular Weight:650.713
Hs Code.:

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

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

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

There total 15 articles about (2S,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-5-iodopentane 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: 80.0%

: 501015-56-1
(2S,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methylpentan-5-ol

: 501015-57-2
(2S,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-5-iodopentane

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene;
DOI:10.1002/anie.200290042

Reference yield:

: 501015-47-0
(2R,3S)-(-)-tert-butyl-(3-methoxymethoxy-2,4-dimethylpent-4-enyloxy)dimethylsilane

: 501015-57-2
(2S,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-5-iodopentane

Guidance literature:: Multi-step reaction with 7 steps

1.1: ozone / CH₂Cl₂ / 1 h / -78 °C

1.2: 86 percent / PPh₃ / CH₂Cl₂ / 0.75 h / -78 °C

2.1: 93 percent / Et₃N / diethyl ether / 3 h / 20 °C

3.1: SnCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

4.1: 11 percent / LiI; LiAlH₄ / diethyl ether / 5 h / -100 °C

5.1: 77 percent / KHMDS / tetrahydrofuran / 20 °C

6.1: 73 percent / aq. p-TsOH / methanol / 1 h

7.1: 80 percent / imidazol; triphenylphosphine; I₂ / toluene / 1 h

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

Reference yield:

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

: 501015-57-2
(2S,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-5-iodopentane

Guidance literature:: Multi-step reaction with 8 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: 11 percent / LiI; LiAlH₄ / diethyl ether / 5 h / -100 °C

6.1: 77 percent / KHMDS / tetrahydrofuran / 20 °C

7.1: 73 percent / aq. p-TsOH / methanol / 1 h

8.1: 80 percent / imidazol; triphenylphosphine; I₂ / toluene / 1 h

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