[(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile

Base Information

Chemical Name:[(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile
CAS No.:262615-00-9
Molecular Formula:C₃₃H₅₆BrNO₆Si₂
Molecular Weight:698.886
Hs Code.:

[(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile

Synonyms:[(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile

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Chemical Property of [(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile

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Technology Process of [(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile

There total 11 articles about [(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile 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: 100.0%

: 151-50-8
potassium cyanide

: 262614-85-7
(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane

: 262615-00-9
[(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile

Guidance literature:: In N,N-dimethyl-formamide; at 65 ℃; for 36h;
DOI:10.1021/ol0000049

Reference yield: 100.0%

: potassium cyanide

: 262614-85-7
(2R,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-iodomethyl-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undecane

: 262615-00-9
[(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile

Guidance literature:: In N,N-dimethyl-formamide; at 20 - 65 ℃; for 36h;
DOI:10.1135/cccc2008181

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 262615-00-9
[(2S,4S,6R,8S,10S)-8-[2-(2-Bromo-benzyloxy)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-4-methyl-10-(2-trimethylsilanyl-ethoxymethoxy)-1,7-dioxa-spiro[5.5]undec-2-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / DIPEA / CH₂Cl₂ / -40 - 0 °C

2: 90 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C

3: 82 percent / I₂; PPh₃; imidazole / benzene / 1.5 h / 20 °C

4: 100 percent / dimethylformamide / 36 h / 65 °C

With 1H-imidazole; water; iodine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide; benzene; 1: Condensation / 2: Hydrolysis / 3: Substitution / 4: Substitution;
DOI:10.1021/ol0000049