(1R,2R,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexan-1-ol

Base Information

Chemical Name:(1R,2R,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexan-1-ol
CAS No.:870862-58-1
Molecular Formula:C₂₇H₃₈O₅Si
Molecular Weight:470.681
Hs Code.:

Synonyms:(1R,2R,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexan-1-ol

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Chemical Property of (1R,2R,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexan-1-ol

Chemical Property:

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Technology Process of (1R,2R,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexan-1-ol

There total 12 articles about (1R,2R,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexan-1-ol 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:

: 870862-48-9
(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol

: 870862-58-1
(1R,2R,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / NaH / various solvent(s); tetrahydrofuran / 4 h / 0 °C

2: 72 percent / acetic acid / H₂O / 4.5 h / 50 °C

3: NaIO₄ / tetrahydrofuran; H₂O / 1.5 h / 20 °C

4: 3.04 g / tetrahydrofuran / 2 h / -20 °C

5: 84 percent / Grubbs' second generation catalyst / toluene / 1.5 h / 80 °C

6: 95 percent / H₂ / Pd/C / ethyl acetate / 21 h / 20 °C

With sodium periodate; hydrogen; sodium hydride; acetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate; toluene;
DOI:10.1021/jo051686m

Reference yield:

: 870862-51-4
(2S,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxy-5-hexenal

: 870862-58-1
(1R,2R,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexan-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 3.04 g / tetrahydrofuran / 2 h / -20 °C

2: 84 percent / Grubbs' second generation catalyst / toluene / 1.5 h / 80 °C

3: 95 percent / H₂ / Pd/C / ethyl acetate / 21 h / 20 °C

With hydrogen; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; toluene;
DOI:10.1021/jo051686m

Reference yield:

: 870862-49-0
(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-3-methoxy-6-heptene

: 870862-58-1
(1R,2R,3S,4S)-4-(tert-butyldiphenylsilanyloxymethyl)-3,4-O-isopropylidenedioxy-2-methoxycyclohexan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / acetic acid / H₂O / 4.5 h / 50 °C

2: NaIO₄ / tetrahydrofuran; H₂O / 1.5 h / 20 °C

3: 3.04 g / tetrahydrofuran / 2 h / -20 °C

4: 84 percent / Grubbs' second generation catalyst / toluene / 1.5 h / 80 °C

5: 95 percent / H₂ / Pd/C / ethyl acetate / 21 h / 20 °C

With sodium periodate; hydrogen; acetic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate; toluene;
DOI:10.1021/jo051686m