(2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)non-5'-enyl)tetrahydrofuran

Base Information

Chemical Name:(2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)non-5'-enyl)tetrahydrofuran
CAS No.:292820-07-6
Molecular Formula:C₄₁H₅₈O₆Si
Molecular Weight:674.993
Hs Code.:

Synonyms:(2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)non-5'-enyl)tetrahydrofuran

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Chemical Property of (2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)non-5'-enyl)tetrahydrofuran

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Technology Process of (2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)non-5'-enyl)tetrahydrofuran

There total 5 articles about (2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)non-5'-enyl)tetrahydrofuran 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: 87.0%

: 80810-40-8
1-(4'-Oxobutyl)-2,3,4,5-tetramethoxy-6-methylbenzene

: {5-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-pentyl}-triphenyl-phosphonium; iodide

: 292820-07-6
(2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)non-5'-enyl)tetrahydrofuran

Guidance literature:: {5-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-pentyl}-triphenyl-phosphonium; iodide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.333333h;

1-(4'-Oxobutyl)-2,3,4,5-tetramethoxy-6-methylbenzene; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1002/1521-3773(20000616)39:12<2099::AID-ANIE2099>3.0.CO;2-Y

Reference yield:

: 35896-58-3
2,3,4,5-tetramethoxytoluene

: 292820-07-6
(2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)non-5'-enyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: nBuLi; TMEDA / hexane / 0.5 h / 0 °C

1.2: 63 percent / tetrahydrofuran / 2 h

2.1: 72 percent / LiAlH₄ / tetrahydrofuran / 3 h

3.1: 88 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 12 h

4.1: 78 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 2.5 h / -40 °C

5.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

5.2: 87 percent / tetrahydrofuran / 1 h / 0 °C

With triethylsilane; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Metallation / 1.2: Acylation / 2.1: Reduction / 3.1: Reduction / 4.1: Oxidation / 5.1: Metallation / 5.2: Condensation;
DOI:10.1002/1521-3773(20000616)39:12<2099::AID-ANIE2099>3.0.CO;2-Y

Reference yield:

: 80810-55-5
1-(4'-Hydroxybutyl)-2,3,4,5-tetramethoxy-6-methylbenzene

: 292820-07-6
(2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)non-5'-enyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1.1: 78 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 2.5 h / -40 °C

2.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

2.2: 87 percent / tetrahydrofuran / 1 h / 0 °C

With oxalyl dichloride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Oxidation / 2.1: Metallation / 2.2: Condensation;
DOI:10.1002/1521-3773(20000616)39:12<2099::AID-ANIE2099>3.0.CO;2-Y