(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol

Base Information

Chemical Name:(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol
CAS No.:852064-97-2
Molecular Formula:C₁₈H₃₈O₄Si₂
Molecular Weight:374.668
Hs Code.:

Synonyms:(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol

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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 (5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol

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Technology Process of (5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol

There total 5 articles about (5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol 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:

: 852064-96-1
2,2-Dimethyl-propionic acid (5S,6S)-5,6-bis-(tert-butyl-dimethyl-silanyloxy)-4-(2,2-dimethyl-propionyloxy)-cyclohex-2-enyl ester

: 852064-97-2
(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 4h;
DOI:10.1021/ol050105c

Reference yield:

: 852064-74-5
1-[(4S,5S)-5-(1-Hydroxy-allyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-prop-2-en-1-ol

: 852064-97-2
(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / Grubbs second-generation catalyst / CH₂Cl₂ / 2 h / Heating

2: 1.67 g / Et₃N / CH₂Cl₂ / 96 h / Heating

3: 437 mg / TFA / H₂O / 1.5 h / 0 °C

4: 537 mg / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

5: 258 mg / DIBAL-H / toluene; CH₂Cl₂ / 4 h / -78 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; water; toluene; 1: ring-closing metathesis;
DOI:10.1021/ol050105c

Reference yield:

: 852064-95-0
2,2-Dimethyl-propionic acid (5R,6R)-4-(2,2-dimethyl-propionyloxy)-5,6-dihydroxy-cyclohex-2-enyl ester

: 852064-97-2
(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 537 mg / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

2: 258 mg / DIBAL-H / toluene; CH₂Cl₂ / 4 h / -78 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In dichloromethane; toluene;
DOI:10.1021/ol050105c