(S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol

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Chemical Name:(S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol
CAS No.:1227307-09-6
Molecular Formula:C₃₈H₅₀O₅Si
Molecular Weight:614.897
Hs Code.:

Synonyms:(S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol

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Chemical Property of (S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol

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Technology Process of (S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol

There total 26 articles about (S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-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: 61.0%

: 1227307-10-9
tert-butyl-(2-((2R,6S)-6-((E)-2-iodoprop-1-enyl)-4-methylenetetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

: 80910-01-6,108836-41-5,134733-19-0,144069-33-0
(S)-2-[(4-methoxybenzyloxy)methyl]oxirane

: 1227307-09-6
(S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol

Guidance literature:: tert-butyl-(2-((2R,6S)-6-((E)-2-iodoprop-1-enyl)-4-methylenetetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane; With tert.-butyl lithium; In toluene; pentane; at -78 ℃; Inert atmosphere;

(S)-2-[(4-methoxybenzyloxy)methyl]oxirane; With boron trifluoride diethyl etherate; In toluene; pentane; at -90 - 20 ℃; Inert atmosphere;

With water; sodium hydrogencarbonate; In toluene; pentane;
DOI:10.1021/ol100665m

Reference yield: 57.0%

: 1437313-06-8
(S,E)-5-((2S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-4-methylpent-4-ene-1,2-diol

: 824-94-2
p-methoxybenzyl chloride

: 1227307-09-6
(S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol

Guidance literature:: (S,E)-5-((2S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-4-methylpent-4-ene-1,2-diol; With di(n-butyl)tin oxide; In toluene; at 140 ℃; for 36h; Dean-Stark;

p-methoxybenzyl chloride; With tetra-(n-butyl)ammonium iodide; at 120 ℃; for 1.5h;
DOI:10.1002/chem.201202553

Reference yield:

: C₂₅H₃₂O₃Si

: 1227307-09-6
(S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol

: C₃₈H₅₀O₅Si

Guidance literature:: Multi-step reaction with 2 steps

1: tetrahydrofuran / 16 h / 40 °C

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 9 h / Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; 1: Wittig reaction;
DOI:10.1002/ejoc.201200286