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

Base Information

Chemical Name: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
CAS No.:882039-13-6
Molecular Formula:C₂₄H₃₈O₃Si
Molecular Weight:402.649
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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:

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

: 4009-98-7
(methoxymethyl)triphenylphosphonium chloride

: 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

Guidance literature:: (methoxymethyl)triphenylphosphonium chloride; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

(2R,4S,5R,6S)-2,4,6-trimethyl-5-({[4-(methyloxy)phenyl]methyl}oxy)-8-(trimethylsilyl)oct-7-ynal; In tetrahydrofuran; at -78 - 20 ℃; for 2.5h;
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

: 882039-13-6
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

Guidance literature:: Multi-step reaction with 4 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

With 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; 4.2: Wittig reaction;
DOI:10.1021/ol052917e

Reference yield:

: 882039-12-5
(2R,4S,5R,6S)-2,4,6-trimethyl-5-({[4-(methyloxy)phenyl]methyl}oxy)-8-(trimethylsilyl)oct-7-yn-1-ol

: 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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; sodium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 2.2: Wittig reaction;
DOI:10.1021/ol052917e