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

Base Information

Chemical Name:(2R,3S,4S)-O-phenyl-3-[1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-hexyl]thiocarbonate
CAS No.:756899-96-4
Molecular Formula:C₃₈H₄₆O₄SSi
Molecular Weight:626.932
Hs Code.:

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

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Chemical Property of (2R,3S,4S)-O-phenyl-3-[1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-hexyl]thiocarbonate

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Technology Process of (2R,3S,4S)-O-phenyl-3-[1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-hexyl]thiocarbonate

There total 3 articles about (2R,3S,4S)-O-phenyl-3-[1-benzyloxy-2,4-dimethyl-6-(tert-butyldiphenylsilyloxy)-hexyl]thiocarbonate 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: 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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

3.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

3.2: 87 percent / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 78 percent / imidazole / dimethylformamide / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

2.2: 87 percent / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.014