(3R,4E,6R,8S,9Z)-methyl 8-(benzyloxymethoxy)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-12-phenyldodeca-4,9-dienoate

Base Information

Chemical Name:(3R,4E,6R,8S,9Z)-methyl 8-(benzyloxymethoxy)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-12-phenyldodeca-4,9-dienoate
CAS No.:947597-01-5
Molecular Formula:C₃₇H₅₆O₇Si
Molecular Weight:640.933
Hs Code.:

Synonyms:(3R,4E,6R,8S,9Z)-methyl 8-(benzyloxymethoxy)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-12-phenyldodeca-4,9-dienoate

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Chemical Property of (3R,4E,6R,8S,9Z)-methyl 8-(benzyloxymethoxy)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-12-phenyldodeca-4,9-dienoate

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Technology Process of (3R,4E,6R,8S,9Z)-methyl 8-(benzyloxymethoxy)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-12-phenyldodeca-4,9-dienoate

There total 11 articles about (3R,4E,6R,8S,9Z)-methyl 8-(benzyloxymethoxy)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-12-phenyldodeca-4,9-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:

: 947596-89-6
(3R,6R,8S,E)-methyl 8-(benzyloxymethoxy)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-12-phenyldodec-4-en-9-ynoate

: 947597-01-5
(3R,4E,6R,8S,9Z)-methyl 8-(benzyloxymethoxy)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-12-phenyldodeca-4,9-dienoate

Guidance literature:: With quinoline; hydrogen; Lindlar's catalyst; In benzene; for 2h;
DOI:10.1021/ja073590a

Reference yield:

: 947596-75-0
(3R,6R,E)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-methylnona-4,8-dien-1-one

: 947597-01-5
(3R,4E,6R,8S,9Z)-methyl 8-(benzyloxymethoxy)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-12-phenyldodeca-4,9-dienoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: K₂CO₃ / 6 h / 0 - 20 °C

2.1: OsO₄; aq. NMO / acetone; tetrahydrofuran; 2-methyl-propan-2-ol / 0 - 20 °C

3.1: NaIO₄ / tetrahydrofuran / 1 h / 0 °C / pH 7

4.1: Zn(OTf)2; (-)-N-Me-ephedrine; Et₃N / toluene / 0.5 h / 20 °C

4.2: toluene / 0.33 h / 20 °C

5.1: NaHMDS / tetrahydrofuran; dimethylformamide / 0.5 h / -78 °C

6.1: H₂; quinoline / Pd/CaCO₃ / benzene / 2 h

With quinoline; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; (-)-N-methylephedrine; hydrogen; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; potassium carbonate; triethylamine; Lindlar's catalyst; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja073590a

Reference yield:

: 947596-99-8
(3R,6R,E)-methyl 3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-8-oxooct-4-enoate

: 947597-01-5
(3R,4E,6R,8S,9Z)-methyl 8-(benzyloxymethoxy)-3-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-5-methyl-12-phenyldodeca-4,9-dienoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: Zn(OTf)2; (-)-N-Me-ephedrine; Et₃N / toluene / 0.5 h / 20 °C

1.2: toluene / 0.33 h / 20 °C

2.1: NaHMDS / tetrahydrofuran; dimethylformamide / 0.5 h / -78 °C

3.1: H₂; quinoline / Pd/CaCO₃ / benzene / 2 h

With quinoline; (-)-N-methylephedrine; hydrogen; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; triethylamine; Lindlar's catalyst; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja073590a