(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one

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Chemical Name:(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one
CAS No.:617715-10-3
Molecular Formula:C₃₉H₇₂O₈Si₂
Molecular Weight:725.167
Hs Code.:

(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one

Synonyms:(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one

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Chemical Property of (2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one

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Technology Process of (2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one

There total 5 articles about (2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one 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: 84.0%

: 617714-97-3
(2R,6S)-2-[(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-oxodecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-4-one

: 617715-10-3
(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃; for 1.5h;
DOI:10.1002/anie.200351817

Reference yield:

: 617715-09-0
(2S,6R)-2-[(2R,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-methylenedecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-4-methylenetetrahydropyran

: 617715-10-3
(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one

Guidance literature:: Multi-step reaction with 3 steps

1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 16 h

2: NaIO₄ / tetrahydrofuran; aq. phosphate buffer / 16 h / pH 7

3: 84 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 1.5 h / -78 °C

With sodium periodate; osmium(VIII) oxide; L-Selectride; 4-methylmorpholine N-oxide; In tetrahydrofuran; phosphate buffer; water; acetone;
DOI:10.1002/anie.200351817

Reference yield:

: 617714-96-2
(2R,5S,8S)-8,10-bis(tert-butyldimethylsilyloxy)-1-((2S,6R)-6-(2-(4-methoxybenzyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-5-methyl-4-methylenedecan-2-ol

: 617715-10-3
(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / proton sponge; 4-Angstroem molecular sieves / CH₂Cl₂

2: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 16 h

3: NaIO₄ / tetrahydrofuran; aq. phosphate buffer / 16 h / pH 7

4: 84 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 1.5 h / -78 °C

With sodium periodate; osmium(VIII) oxide; Proton Sponge; 4 A molecular sieve; L-Selectride; 4-methylmorpholine N-oxide; In tetrahydrofuran; phosphate buffer; dichloromethane; water; acetone;
DOI:10.1002/anie.200351817