(2R,3S,4S)-1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-3-hexanol

Base Information

Chemical Name:(2R,3S,4S)-1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-3-hexanol
CAS No.:756899-95-3
Molecular Formula:C₃₁H₄₂O₃Si
Molecular Weight:490.758
Hs Code.:

Synonyms:(2R,3S,4S)-1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-3-hexanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S,4S)-1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-3-hexanol

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Technology Process of (2R,3S,4S)-1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-3-hexanol

There total 2 articles about (2R,3S,4S)-1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-3-hexanol 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: 78.0%

: 134961-82-3
(2R,3S,4S)-1-benzyloxy-2,4-dimethyl-3,6-hexanediol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 756899-95-3
(2R,3S,4S)-1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-3-hexanol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1016/j.tet.2004.06.014

Reference yield:

: 108814-35-3
(2R,3R,4S)-1-(benzyloxy)-2,4-dimethyl-3-hydroxy-5-hexene

: 756899-95-3
(2R,3S,4S)-1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-3-hexanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 0.67 h / sonication

1.2: 91 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -5 °C

2.1: 78 percent / imidazole / dimethylformamide / 0 - 20 °C

With 1H-imidazole; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.014

Reference yield: 87.0%

: 1005-56-7
phenylcarbonochloridothioate

: 756899-95-3
(2R,3S,4S)-1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-3-hexanol

: 756899-96-4
(2R,3S,4S)-O-phenyl-3-[1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-hexyl]thiocarbonate

Guidance literature:: (2R,3S,4S)-1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-3-hexanol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

phenylcarbonochloridothioate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1.25h; Further stages.;
DOI:10.1016/j.tet.2004.06.014