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

Base Information

Chemical Name:(5R,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-dione
CAS No.:852064-84-7
Molecular Formula:C₁₈H₃₄O₄Si₂
Molecular Weight:370.637
Hs Code.:

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

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Chemical Property of (5R,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-dione

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

There total 6 articles about (5R,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-dione 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: 93.0%

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

: 852064-84-7
(5R,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-dione

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 1h;
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

: 852064-84-7
(5R,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-dione

Guidance literature:: Multi-step reaction with 6 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

6: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

With 2,6-dimethylpyridine; diisobutylaluminium hydride; Dess-Martin periodane; 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

: 852064-84-7
(5R,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-dione

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

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