tert-butyl {(R,2E,7E,9E)-6-[(4-methoxybenzyl)oxy]-4,4,6,9-tetramethyl-12-(trimethylsilyl)dodeca-2,7,9-trien-11-yn-1-yloxy}dimethylsilane

Base Information

• Chemical Name: tert-butyl {(R,2E,7E,9E)-6-[(4-methoxybenzyl)oxy]-4,4,6,9-tetramethyl-12-(trimethylsilyl)dodeca-2,7,9-trien-11-yn-1-yloxy}dimethylsilane
• CAS No.: 1309113-26-5
• Molecular Formula: C₃₃H₅₄O₃Si₂
• Molecular Weight: 554.961

Synonyms:tert-butyl {(R,2E,7E,9E)-6-[(4-methoxybenzyl)oxy]-4,4,6,9-tetramethyl-12-(trimethylsilyl)dodeca-2,7,9-trien-11-yn-1-yloxy}dimethylsilane

Chemical Property of tert-butyl {(R,2E,7E,9E)-6-[(4-methoxybenzyl)oxy]-4,4,6,9-tetramethyl-12-(trimethylsilyl)dodeca-2,7,9-trien-11-yn-1-yloxy}dimethylsilane

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of tert-butyl {(R,2E,7E,9E)-6-[(4-methoxybenzyl)oxy]-4,4,6,9-tetramethyl-12-(trimethylsilyl)dodeca-2,7,9-trien-11-yn-1-yloxy}dimethylsilane

There total 25 articles about tert-butyl {(R,2E,7E,9E)-6-[(4-methoxybenzyl)oxy]-4,4,6,9-tetramethyl-12-(trimethylsilyl)dodeca-2,7,9-trien-11-yn-1-yloxy}dimethylsilane 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: 84.0%

(E)-diethyl (2-methyl-5-(trimethylsilyl)pent-2-en-4-yn-1-yl)phosphonate (854490-31-6) + (R,E)-7-[(tert-butyldimethylsilyl)oxy]-2-[(4-methoxybenzyl)oxy]-2,4,4-trimethylhept-5-enal (1309113-25-4) → tert-butyl {(R,2E,7E,9E)-6-[(4-methoxybenzyl)oxy]-4,4,6,9-tetramethyl-12-(trimethylsilyl)dodeca-2,7,9-trien-11-yn-1-yloxy}dimethylsilane (1309113-26-5)

Guidance literature:

(E)-diethyl (2-methyl-5-(trimethylsilyl)pent-2-en-4-yn-1-yl)phosphonate; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 1h;

(R,E)-7-[(tert-butyldimethylsilyl)oxy]-2-[(4-methoxybenzyl)oxy]-2,4,4-trimethylhept-5-enal; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ol403441c

Reference yield: 84.0%

(E)-diethyl (2-methyl-5-(trimethylsilyl)pent-2-en-4-yn-1-yl)phosphonate (854490-31-6) + (R,E)-7-[(tert-butyldimethylsilyl)oxy]-2-[(4-methoxybenzyl)oxy]-2,4,4-trimethylhept-5-enal (1309113-25-4) → tert-butyl{(R,2E,9E)-6-[(4-methoxybenzyl)oxy-4,4,6,9-tetramethyl-12-(trimethylsilyl)dodeca-2,7,9-trien-11-yn-1-yl]oxy}dimethylsilane + tert-butyl {(R,2E,7E,9E)-6-[(4-methoxybenzyl)oxy]-4,4,6,9-tetramethyl-12-(trimethylsilyl)dodeca-2,7,9-trien-11-yn-1-yloxy}dimethylsilane (1309113-26-5)

Guidance literature:

(E)-diethyl (2-methyl-5-(trimethylsilyl)pent-2-en-4-yn-1-yl)phosphonate; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

(R,E)-7-[(tert-butyldimethylsilyl)oxy]-2-[(4-methoxybenzyl)oxy]-2,4,4-trimethylhept-5-enal; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201006880

Reference yield:

(E)-tert-butyl[(6-{[(4-methoxybenzyl)oxy]methyl}-4,4-dimethylhepta-2,6-dien-1-yl)oxy]dimethylsilane (1309113-14-1) → tert-butyl {(R,2E,7E,9E)-6-[(4-methoxybenzyl)oxy]-4,4,6,9-tetramethyl-12-(trimethylsilyl)dodeca-2,7,9-trien-11-yn-1-yloxy}dimethylsilane (1309113-26-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 20 h / -25 °C

2.2: Molecular sieve

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h

4.1: PPTA / dichloromethane / 2 h / 20 °C

4.2: -78 - 20 °C

5.1: dmap; sodium hydrogencarbonate / dichloromethane / 3 h / 0 °C

6.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C

6.2: -78 - 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; potassium hexamethylsilazane; sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol403441c

upstream raw materials:

(E)-1-bromo-2-methyl-5-(trimethylsilyl)pent-2-en-4-yne

(E)-diethyl (2-methyl-5-(trimethylsilyl)pent-2-en-4-yn-1-yl)phosphonate

(R,E)-7-[(tert-butyldimethylsilyl)oxy]-2-[(4-methoxybenzyl)oxy]-2,4,4-trimethylhept-5-enal

(E)-7-[(tert-butyldimethylsilyl)oxy]-4,4-dimethyl-2-methylenehept-5-en-1-ol

Downstream raw materials:

(1R,3aS,4R,5S,7aR)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone

(1R,3aR,4S,5R,7aS)-5-ethynyl-1-[(4-methoxybenzyl)oxy-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl][4-(trimethylsilyl)phenyl]methanone

(R,2E,7E,9E)-6-[(4-methoxybenzyl)oxy]-4,4,6,9-tetramethyldodeca-2,7,9-trien-11-yn-1-ol

[4-(benzyldimethylsilyl)phenyl]{(1R,3aS,4R,5S,7aR)-5-ethynyl-1-[(4-methoxybenzyl)oxy]-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}methanone

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