(1R,2S,3R)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol

Base Information

• Chemical Name: (1R,2S,3R)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol
• CAS No.: 152492-32-5
• Molecular Formula: C₂₈H₄₀O₂Si
• Molecular Weight: 436.71
• Mol file: 152492-32-5.mol

Synonyms:(1R,2S,3R)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol

Chemical Property of (1R,2S,3R)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol

There total 27 articles about (1R,2S,3R)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol 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: 82.0%

methyllithium (917-54-4) + (2S,3R)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone (146383-52-0) → (1R,2S,3R)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol (152492-32-5)

Guidance literature:

In diethyl ether; at -78 ℃; for 0.583333h;

DOI:10.1021/jo00075a021

Reference yield:

C15H20O6 → (1R,2S,3R)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol (152492-32-5)

Guidance literature:

Multi-step reaction with 11 steps

1: NaBH₄ / methanol / 0.67 h / 0 °C

2: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

3: 77 percent / 60percent aq. TFA / 72 h / 5 °C

4: aq. NaIO₄ / methanol / 4 h / Ambient temperature

5: conc. aq. HCl / 72 h / -15 °C

6: 52 percent / Raney nickel T-4 / ethanol / 13 h / Heating

7: aq. NaIO₄ / methanol / 1 h / Ambient temperature

8: tetrahydrofuran / 0.17 h / Ambient temperature

9: 100 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

10: 1.) imidazole, 2.) PCC, molecular sieves / 1.) DMF, r.t., 1 h, 2.) CH₂Cl₂, r.t., 1 h

11: 82 percent / diethyl ether / 0.58 h / -78 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; molecular sieve; Raney nickel T-4; sodium hydride; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00075a021

Reference yield:

(2'S,3aS,3'R,4'R,5'R,7aR)-2'-(Hydroxymethyl)-4',5'-(isopropylidenedioxy)spiro-2(3H)-one → (1R,2S,3R)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol (152492-32-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

2: 77 percent / 60percent aq. TFA / 72 h / 5 °C

3: aq. NaIO₄ / methanol / 4 h / Ambient temperature

4: conc. aq. HCl / 72 h / -15 °C

5: 52 percent / Raney nickel T-4 / ethanol / 13 h / Heating

6: aq. NaIO₄ / methanol / 1 h / Ambient temperature

7: tetrahydrofuran / 0.17 h / Ambient temperature

8: 100 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

9: 1.) imidazole, 2.) PCC, molecular sieves / 1.) DMF, r.t., 1 h, 2.) CH₂Cl₂, r.t., 1 h

10: 82 percent / diethyl ether / 0.58 h / -78 °C

With 1H-imidazole; hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; molecular sieve; Raney nickel T-4; sodium hydride; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00075a021

upstream raw materials:

methyllithium

(2S,3R)-3-Methyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanone

(2R,3R,4R,5S)-4-(2-hydroxyethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

(1R,2S,3R)-2-(2-Hydroxyethyl)-3-methyl-3-vinylcyclohexanol

Downstream raw materials:

(1R,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol