(3R,5S,6R,7S)-3,5,7-trimethyl-6-({[4-(methyloxy)phenyl]methyl}oxy)-9-(trimethylsilyl)non-8-yn-1-ol

Base Information

Chemical Name:(3R,5S,6R,7S)-3,5,7-trimethyl-6-({[4-(methyloxy)phenyl]methyl}oxy)-9-(trimethylsilyl)non-8-yn-1-ol
CAS No.:882039-14-7
Molecular Formula:C₂₃H₃₈O₃Si
Molecular Weight:390.638
Hs Code.:

Synonyms:(3R,5S,6R,7S)-3,5,7-trimethyl-6-({[4-(methyloxy)phenyl]methyl}oxy)-9-(trimethylsilyl)non-8-yn-1-ol

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Chemical Property of (3R,5S,6R,7S)-3,5,7-trimethyl-6-({[4-(methyloxy)phenyl]methyl}oxy)-9-(trimethylsilyl)non-8-yn-1-ol

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Technology Process of (3R,5S,6R,7S)-3,5,7-trimethyl-6-({[4-(methyloxy)phenyl]methyl}oxy)-9-(trimethylsilyl)non-8-yn-1-ol

There total 6 articles about (3R,5S,6R,7S)-3,5,7-trimethyl-6-({[4-(methyloxy)phenyl]methyl}oxy)-9-(trimethylsilyl)non-8-yn-1-ol 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:

: 882039-13-6
trimethyl[(3S,4R,5S,7R)-3,5,7-trimethyl-9-(methyloxy)-4-({[4-(methyloxy)phenyl]methyl}oxy)non-8-en-1-yn-1-yl]silane

: 882039-14-7
(3R,5S,6R,7S)-3,5,7-trimethyl-6-({[4-(methyloxy)phenyl]methyl}oxy)-9-(trimethylsilyl)non-8-yn-1-ol

Guidance literature:: trimethyl[(3S,4R,5S,7R)-3,5,7-trimethyl-9-(methyloxy)-4-({[4-(methyloxy)phenyl]methyl}oxy)non-8-en-1-yn-1-yl]silane; With hydrogenchloride; In water; acetonitrile; at 20 ℃; for 2h;

With sodium tetrahydroborate; In water; acetonitrile; at 20 ℃; for 3h;
DOI:10.1021/ol052917e

Reference yield:

: (3S,5S,7R)-8-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3,5,7-trimethyl-1-(trimethylsilyl)oct-1-yn-4-ol

: 882039-14-7
(3R,5S,6R,7S)-3,5,7-trimethyl-6-({[4-(methyloxy)phenyl]methyl}oxy)-9-(trimethylsilyl)non-8-yn-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / CF₃SO₃H / diethyl ether / 7 h / cooling

2.1: camphorsulfonic acid / methanol / 2 h / 20 °C

3.1: PhI(OAc)2; TEMPO / CH₂Cl₂ / 1.5 h / 25 °C

4.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

4.2: tetrahydrofuran / 2.5 h / -78 - 20 °C

5.1: hydrochloric acid / acetonitrile; H₂O / 2 h / 20 °C

5.2: 500 mg / NaBH₄ / acetonitrile; H₂O / 3 h / 20 °C

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; sodium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile; 4.2: Wittig reaction;
DOI:10.1021/ol052917e

Reference yield:

: 882039-22-7
(2R,4S,5R,6S)-2,4,6-trimethyl-5-({[4-(methyloxy)phenyl]methyl}oxy)-8-(trimethylsilyl)oct-7-ynal

: 882039-14-7
(3R,5S,6R,7S)-3,5,7-trimethyl-6-({[4-(methyloxy)phenyl]methyl}oxy)-9-(trimethylsilyl)non-8-yn-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / 2.5 h / -78 - 20 °C

2.1: hydrochloric acid / acetonitrile; H₂O / 2 h / 20 °C

2.2: 500 mg / NaBH₄ / acetonitrile; H₂O / 3 h / 20 °C

With hydrogenchloride; sodium hexamethyldisilazane; In tetrahydrofuran; water; acetonitrile; 1.2: Wittig reaction;
DOI:10.1021/ol052917e