(4S,6RS)-4,8-Dimethyl-1-furan-3'-ylnonane-1-on-4,6-diol p-methoxybenzylideneacetal

Base Information

Chemical Name:(4S,6RS)-4,8-Dimethyl-1-furan-3'-ylnonane-1-on-4,6-diol p-methoxybenzylideneacetal
CAS No.:247256-63-9
Molecular Formula:C₂₃H₃₀O₅
Molecular Weight:386.488
Hs Code.:

Synonyms:(4S,6RS)-4,8-Dimethyl-1-furan-3'-ylnonane-1-on-4,6-diol p-methoxybenzylideneacetal

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Chemical Property of (4S,6RS)-4,8-Dimethyl-1-furan-3'-ylnonane-1-on-4,6-diol p-methoxybenzylideneacetal

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Technology Process of (4S,6RS)-4,8-Dimethyl-1-furan-3'-ylnonane-1-on-4,6-diol p-methoxybenzylideneacetal

There total 8 articles about (4S,6RS)-4,8-Dimethyl-1-furan-3'-ylnonane-1-on-4,6-diol p-methoxybenzylideneacetal 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: 75.0%

: 82061-00-5
2-Furanyl-2-trimethylsilyloxyacetonitrile

: 247256-62-8
(3R,5RS)-3,7-Dimethyl-1-iodo-3,5-octanediol p-methoxybenzylidenacetal

: 247256-63-9
(4S,6RS)-4,8-Dimethyl-1-furan-3'-ylnonane-1-on-4,6-diol p-methoxybenzylideneacetal

Guidance literature:: 2-Furanyl-2-trimethylsilyloxyacetonitrile; With methyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h;

(3R,5RS)-3,7-Dimethyl-1-iodo-3,5-octanediol p-methoxybenzylidenacetal; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 3.5h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 0.5h;
DOI:10.1002/(SICI)1521-3765(19991001)5:10<2885::AID-CHEM2885>3.0.CO;2-8

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 247256-63-9
(4S,6RS)-4,8-Dimethyl-1-furan-3'-ylnonane-1-on-4,6-diol p-methoxybenzylideneacetal

Guidance literature:: Multi-step reaction with 4 steps

1.1: 86 percent / p-TsOH / CH₂Cl₂ / 1 h / 20 °C

2.1: 99 percent / TBAF*3H₂O / tetrahydrofuran / 5 h / 20 °C

3.1: 87 percent / I₂; imidazole; PPh₃ / diethyl ether; acetonitrile / 12 h / 20 °C

4.1: MeLi / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C

4.2: diethyl ether; tetrahydrofuran / 3.5 h / -78 - 20 °C

4.3: 75 percent / TBAF*3H₂O / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; methyllithium; iodine; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 1.1: Cyclization / 2.1: Hydrolysis / 3.1: Substitution / 4.1: Metallation / 4.2: Substitution / 4.3: Elimination;
DOI:10.1002/(SICI)1521-3765(19991001)5:10<2885::AID-CHEM2885>3.0.CO;2-8

Reference yield:

: 214959-70-3
(3S,1'S,2'S)-1-tert-Butyldiphenylsiloxy-3-methyl-3-(1'-phenyl-2'-trifluoroacetamido-1'-propoxy)hex-5-en

: 247256-63-9
(4S,6RS)-4,8-Dimethyl-1-furan-3'-ylnonane-1-on-4,6-diol p-methoxybenzylideneacetal

Guidance literature:: Multi-step reaction with 7 steps

1.1: O₃ / CH₂Cl₂; methanol / -78 °C

1.2: 95 percent / PPh₃ / 0.5 h / -78 °C

2.1: 96 percent / tetrahydrofuran; diethyl ether / 4 h / -78 - 20 °C

3.1: 95 percent / Na; NH₃ / tetrahydrofuran / 0.5 h / -78 °C

4.1: 86 percent / p-TsOH / CH₂Cl₂ / 1 h / 20 °C

5.1: 99 percent / TBAF*3H₂O / tetrahydrofuran / 5 h / 20 °C

6.1: 87 percent / I₂; imidazole; PPh₃ / diethyl ether; acetonitrile / 12 h / 20 °C

7.1: MeLi / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C

7.2: diethyl ether; tetrahydrofuran / 3.5 h / -78 - 20 °C

7.3: 75 percent / TBAF*3H₂O / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; ammonia; methyllithium; iodine; sodium; toluene-4-sulfonic acid; ozone; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 1.1: Oxidation / 1.2: Reduction / 2.1: Grignard reaction / 3.1: Substitution / 4.1: Cyclization / 5.1: Hydrolysis / 6.1: Substitution / 7.1: Metallation / 7.2: Substitution / 7.3: Elimination;
DOI:10.1002/(SICI)1521-3765(19991001)5:10<2885::AID-CHEM2885>3.0.CO;2-8