methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(E)-dienoate

Base Information

Chemical Name:methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(E)-dienoate
CAS No.:218269-05-7
Molecular Formula:C₃₂H₃₈O₃Si
Molecular Weight:498.737
Hs Code.:

Synonyms:methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(E)-dienoate

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Chemical Property of methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(E)-dienoate

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Technology Process of methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(E)-dienoate

There total 15 articles about methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(E)-dienoate 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: 41.0%

: (E)-(5S,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid methyl ester

: 218269-05-7
methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(E)-dienoate

Guidance literature:: With dmap; triethylamine; Methanesulfonic anhydride; In dichloromethane; for 120h;
DOI:10.1016/S0040-4039(98)01784-5

Reference yield:

: 1449-46-3
benzyltriphenylphosphonium bromide

: 186193-13-5
methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate

: 218269-05-7
methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(E)-dienoate

: methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(Z)-dienoate

Guidance literature:: benzyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h;

methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-7-oxohept-2(E)-enoate; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

With 2,2'-azobis(isobutyronitrile); thiophenol; In benzene; for 3h; Heating;
DOI:10.1021/jo026802p

Reference yield:

: 186193-01-1
(3R,4R)-4-methylhept-5(E)-en-1-yn-3-ol

: 218269-05-7
methyl (5S,6R)-5-<(tert-butyldiphenylsilyl)oxy>-6-methyl-8-phenyl-octa-2(E),7(E)-dienoate

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / imidazole / dimethylformamide

2: 1.) 2-methyl-2-butene, BH₃, 2.) H₂O₂, KH₂PO₄, K₂HPO₄ / 1.) THF, -50 deg C to rt, 1 h, 2.) THF, H₂O, 0 deg C, 1 h

3: 92 percent / tetramethylguanidine / tetrahydrofuran / 4.5 h / -78 - 20 °C

4: 1.) O₃, 2.) Zn, AcOH / 1.) pyridine, CH₂Cl₂, -78 deg C, 2.) pyridine, CH₂Cl₂, -78 to 25 deg C

With 1H-imidazole; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; 2-methyl-but-2-ene; 1,1,3,3-tetramethylguanidine; borane; dihydrogen peroxide; ozone; acetic acid; zinc; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo9815958