(1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol

Base Information

Chemical Name:(1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol
CAS No.:338460-92-7
Molecular Formula:C₁₄H₂₈O₄Si
Molecular Weight:288.459
Hs Code.:

Synonyms:(1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol

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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 (1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol

Chemical Property:

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Technology Process of (1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol

There total 5 articles about (1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-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: 94.0%

: 338460-83-6
dimethyl (1S,2R,5S)-5-tert-butyldimethylsilyloxy-2-hydroxy-3-cyclohexene-1,2-dicarboxylate

: 338460-92-7
(1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 3h;
DOI:10.1016/j.carres.2011.04.011

Reference yield:

: 496-64-0
3-hydroxy-2-pyrone

: 338460-92-7
(1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 4 steps

1: cinchonine / water; isopropyl alcohol / 2 h / 0 °C

2: methanol / 0.33 h

3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 60 °C

4: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; cinchonine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; isopropyl alcohol; 1: Diels-Alder reaction;
DOI:10.1016/j.carres.2011.04.011

Reference yield:

: 203627-51-4
(1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester

: 338460-92-7
(1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 2 steps

1: 74 percent / imidazole / dimethylformamide / 10 h / 60 °C

2: 89 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00032-1