(3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanitrile

Base Information

Chemical Name:(3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanitrile
CAS No.:528864-97-3
Molecular Formula:C₃₂H₄₁NO₂Si
Molecular Weight:499.769
Hs Code.:

Synonyms:(3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanitrile

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Chemical Property of (3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanitrile

Chemical Property:

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Technology Process of (3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanitrile

There total 5 articles about (3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanitrile 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: 98.0%

: 143-33-9,25596-52-5
sodium cyanide

: 528864-95-1
(2R,3R)-7-(benzyloxy)-3-(tert-butyldiphenylsilyloxy)-2-methylheptanol p-toluenesulfonate

: 528864-97-3
(3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanitrile

Guidance literature:: In dimethyl sulfoxide; at 60 ℃; for 20h;
DOI:10.1016/S0040-4020(02)01514-4

Reference yield:

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

: 528864-97-3
(3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanitrile

Guidance literature:: Multi-step reaction with 5 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

With pyridine; 1H-imidazole; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
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

: 528864-97-3
(3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanitrile

Guidance literature:: Multi-step reaction with 4 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

With pyridine; 1H-imidazole; lithium borohydride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)01514-4