(2S,5R)-2-Hydroxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)nonyl)tetrahydrofuran

Base Information

Chemical Name:(2S,5R)-2-Hydroxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)nonyl)tetrahydrofuran
CAS No.:292820-17-8
Molecular Formula:C₂₅H₄₂O₆
Molecular Weight:438.605
Hs Code.:

Synonyms:(2S,5R)-2-Hydroxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)nonyl)tetrahydrofuran

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Chemical Property of (2S,5R)-2-Hydroxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)nonyl)tetrahydrofuran

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Technology Process of (2S,5R)-2-Hydroxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)nonyl)tetrahydrofuran

There total 7 articles about (2S,5R)-2-Hydroxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)nonyl)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: 95.0%

: 292820-16-7
(2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)nonyl)tetrahydrofuran

: 292820-17-8
(2S,5R)-2-Hydroxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)nonyl)tetrahydrofuran

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2.5h;
DOI:10.1002/1521-3773(20000616)39:12<2099::AID-ANIE2099>3.0.CO;2-Y

Reference yield:

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

: 292820-17-8
(2S,5R)-2-Hydroxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)nonyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / H₂ / 5percent Pt/C / ethyl acetate / 6 h / 760.05 Torr

2: 95 percent / TBAF / tetrahydrofuran / 2.5 h

With tetrabutyl ammonium fluoride; hydrogen; 5percent Pt/C; In tetrahydrofuran; ethyl acetate;
DOI:10.1002/1521-3765(20010302)7:5<993::AID-CHEM993>3.0.CO;2-S

Reference yield:

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

: 292820-17-8
(2S,5R)-2-Hydroxymethyl-5-(9'-(2'',3'',4'',5''-tetramethoxy-6''-methylphenyl)nonyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 7 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

6.1: 97 percent / H₂ / ethyl acetate / 6 h

7.1: 95 percent / nBu₄F / tetrahydrofuran / 2.5 h

With triethylsilane; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 1.1: Metallation / 1.2: Acylation / 2.1: Reduction / 3.1: Reduction / 4.1: Oxidation / 5.1: Metallation / 5.2: Condensation / 6.1: Catalytic hydrogenation / 7.1: Silyl ether cleavage;
DOI:10.1002/1521-3773(20000616)39:12<2099::AID-ANIE2099>3.0.CO;2-Y