methyl (5R,6S,7R,8R)-5,7-dihydroxy-6-methyl-8-[(tert-butyldimethylsilyl)oxy]-8-phenyloct-2(E)-enoate

Base Information

Chemical Name:methyl (5R,6S,7R,8R)-5,7-dihydroxy-6-methyl-8-[(tert-butyldimethylsilyl)oxy]-8-phenyloct-2(E)-enoate
CAS No.:288374-78-7
Molecular Formula:C₂₂H₃₆O₅Si
Molecular Weight:408.61
Hs Code.:

Synonyms:methyl (5R,6S,7R,8R)-5,7-dihydroxy-6-methyl-8-[(tert-butyldimethylsilyl)oxy]-8-phenyloct-2(E)-enoate

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Chemical Property of methyl (5R,6S,7R,8R)-5,7-dihydroxy-6-methyl-8-[(tert-butyldimethylsilyl)oxy]-8-phenyloct-2(E)-enoate

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Technology Process of methyl (5R,6S,7R,8R)-5,7-dihydroxy-6-methyl-8-[(tert-butyldimethylsilyl)oxy]-8-phenyloct-2(E)-enoate

There total 8 articles about methyl (5R,6S,7R,8R)-5,7-dihydroxy-6-methyl-8-[(tert-butyldimethylsilyl)oxy]-8-phenyloct-2(E)-enoate 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: 70.0%

: 288374-75-4
methyl (5R,6S,8R)-5-hydroxy-6-methyl-7-oxo-8-[(tert-butyl-dimethylsilyl)oxy]-8-phenyl-oct-2(E)-enoate

: 288374-78-7
methyl (5R,6S,7R,8R)-5,7-dihydroxy-6-methyl-8-[(tert-butyldimethylsilyl)oxy]-8-phenyloct-2(E)-enoate

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at -78 - -30 ℃;
DOI:10.1016/S0040-4020(00)00255-6

Reference yield:

: 611-71-2
(R)-Mandelic Acid

: 288374-78-7
methyl (5R,6S,7R,8R)-5,7-dihydroxy-6-methyl-8-[(tert-butyldimethylsilyl)oxy]-8-phenyloct-2(E)-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / diethyl ether

2.1: Me₃Al / benzene; hexane / 0 - 20 °C

2.2: 93 percent / benzene / 20 °C

3.1: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

4.1: 94 percent / tetrahydrofuran; diethyl ether / 5 h / 0 °C

5.1: diisopropylethylamine; dibutylboron triflate / CH₂Cl₂ / -78 - 0 °C

5.2: 65 percent / CH₂Cl₂ / -78 - 0 °C

6.1: 87 percent / trichloroacetic acid; water / CH₂Cl₂ / 1 h / 20 °C

7.1: LiCl; diisopropylethylamine / acetonitrile / 0.08 h

7.2: 77 percent / acetonitrile / 3 h / 20 °C

8.1: 70 percent / LiBH₄ / tetrahydrofuran / -78 - -30 °C

With lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; water; trimethylaluminum; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; trichloroacetic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile; benzene; 1.1: Methylation / 2.1: Metallation / 2.2: Substitution / 3.1: silylation / 4.1: Grignard reaction / 5.1: Addition / 5.2: Condensation / 6.1: Hydrolysis / 7.1: deprotonation / 7.2: Condensation / 8.1: Reduction;
DOI:10.1016/S0040-4020(00)00255-6

Reference yield:

: 20698-91-3
(R)-methyl mandelate

: 288374-78-7
methyl (5R,6S,7R,8R)-5,7-dihydroxy-6-methyl-8-[(tert-butyldimethylsilyl)oxy]-8-phenyloct-2(E)-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: Me₃Al / benzene; hexane / 0 - 20 °C

1.2: 93 percent / benzene / 20 °C

2.1: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

3.1: 94 percent / tetrahydrofuran; diethyl ether / 5 h / 0 °C

4.1: diisopropylethylamine; dibutylboron triflate / CH₂Cl₂ / -78 - 0 °C

4.2: 65 percent / CH₂Cl₂ / -78 - 0 °C

5.1: 87 percent / trichloroacetic acid; water / CH₂Cl₂ / 1 h / 20 °C

6.1: LiCl; diisopropylethylamine / acetonitrile / 0.08 h

6.2: 77 percent / acetonitrile / 3 h / 20 °C

7.1: 70 percent / LiBH₄ / tetrahydrofuran / -78 - -30 °C

With lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; water; trimethylaluminum; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; trichloroacetic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile; benzene; 1.1: Metallation / 1.2: Substitution / 2.1: silylation / 3.1: Grignard reaction / 4.1: Addition / 4.2: Condensation / 5.1: Hydrolysis / 6.1: deprotonation / 6.2: Condensation / 7.1: Reduction;
DOI:10.1016/S0040-4020(00)00255-6