(5R,6R,8E)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol

Base Information

Chemical Name:(5R,6R,8E)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol
CAS No.:528865-01-2
Molecular Formula:C₃₉H₄₈O₂Si
Molecular Weight:576.894
Hs Code.:

Synonyms:(5R,6R,8E)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol

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Chemical Property of (5R,6R,8E)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol

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Technology Process of (5R,6R,8E)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol

There total 10 articles about (5R,6R,8E)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol 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: 77.0%

: 1080-32-6
O,O-diethyl benzylphosphonate

: 528864-99-5
(3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanal

: 528865-01-2
(5R,6R,8E)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol

Guidance literature:: With 15-crown-5; sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1016/S0040-4020(02)01514-4

Reference yield:

: 78999-24-3
5-benzyloxy-1-pentanal

: 528865-01-2
(5R,6R,8E)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol

Guidance literature:: Multi-step reaction with 8 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

1.2: CH₂Cl₂ / -78 - 20 °C

1.3: 88 percent / aq. H₂O₂ / methanol; CH₂Cl₂; aq. phosphate buffer / 0 - 20 °C

2.1: 81 percent / imidazole / dimethylformamide / 23 h

3.1: 62 percent / LiBH₄ / tetrahydrofuran; methanol / 0 - 20 °C

4.1: 89 percent / pyridine / CH₂Cl₂ / 24 h

5.1: 98 percent / dimethylsulfoxide / 20 h / 60 °C

6.1: DIBAL-H / CH₂Cl₂ / 1.58 h / -78 °C

7.1: 14.5 g / aq. H₂SO₄; aq. NH₄Cl / 0.33 h / 20 °C

With pyridine; 1H-imidazole; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; sulfuric acid; diisobutylaluminium hydride; ammonium chloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 8.1: Julia olefination;
DOI:10.1016/S0040-4020(02)01514-4

Reference yield:

: 528864-90-6
(4S,2'R,3'R)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-isopropyl-1,3-oxazolidin-2-one

: 528865-01-2
(5R,6R,8E)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol

Guidance literature:: Multi-step reaction with 7 steps

1: 81 percent / imidazole / dimethylformamide / 23 h

2: 62 percent / LiBH₄ / tetrahydrofuran; methanol / 0 - 20 °C

3: 89 percent / pyridine / CH₂Cl₂ / 24 h

4: 98 percent / dimethylsulfoxide / 20 h / 60 °C

5: DIBAL-H / CH₂Cl₂ / 1.58 h / -78 °C

6: 14.5 g / aq. H₂SO₄; aq. NH₄Cl / 0.33 h / 20 °C

With pyridine; 1H-imidazole; lithium borohydride; sulfuric acid; diisobutylaluminium hydride; ammonium chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 7: Julia olefination;
DOI:10.1016/S0040-4020(02)01514-4