(4R,5S,10S,11R,12S,14R,2E)-5,11,15-tris(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

Base Information

Chemical Name:(4R,5S,10S,11R,12S,14R,2E)-5,11,15-tris(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one
CAS No.:792921-81-4
Molecular Formula:C₅₆H₈₈O₅Si₃
Molecular Weight:925.568
Hs Code.:

Synonyms:(4R,5S,10S,11R,12S,14R,2E)-5,11,15-tris(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

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Chemical Property of (4R,5S,10S,11R,12S,14R,2E)-5,11,15-tris(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

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Technology Process of (4R,5S,10S,11R,12S,14R,2E)-5,11,15-tris(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

There total 37 articles about (4R,5S,10S,11R,12S,14R,2E)-5,11,15-tris(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one 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: 93.0%

: 792921-69-8
(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,4-dimethyl-7-(trityloxy)hept-5-enamide

: 792921-81-4
(4R,5S,10S,11R,12S,14R,2E)-5,11,15-tris(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

Guidance literature:: (3S,4R,5S,7R)-4-(tert-butyldimethylsilyloxy)-7-((tert-butyldimethylsilyloxy)methyl)-3,5-dimethyloct-1-yne; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.583333h;

(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,4-dimethyl-7-(trityloxy)hept-5-enamide; In tetrahydrofuran; hexan<6.25 ml; at -78 - 0 ℃; for 0.583333h;

Reference yield: 93.0%

: 792921-69-8
(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,4-dimethyl-7-(trityloxy)hept-5-enamide

: 792921-68-7
(3S,4R,5S,7R)-4-(tert-butyldimethylsilyloxy)-7-((tert-butyldimethylsilyloxy)methyl)-3,5-dimethyloct-1-yne

: 792921-81-4
(4R,5S,10S,11R,12S,14R,2E)-5,11,15-tris(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

Guidance literature:: With n-butyllithium; In tetrahydrofuran;
DOI:10.1002/anie.200460593

Reference yield:

: 792921-80-3
(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol

: 792921-81-4
(4R,5S,10S,11R,12S,14R,2E)-5,11,15-tris(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethyl-1-(trityloxy)pentadec-2-en-8-yn-7-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfur trioxide*pyridine complex; Et₃N; DMSO / CH₂Cl₂ / 0 - 20 °C

2.1: 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / H₂O; tetrahydrofuran / 2 h

3.1: 2.65 g / 4-(dimethylamino)pyridine; Et₃N; DCC / CH₂Cl₂ / 0 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

4.2: 93 percent / tetrahydrofuran; hexane / -78 - 0 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water;
DOI:10.1016/j.tet.2007.05.033