(1R,2S)-trans-2-hydroxy-1-cyanocyclohexane trimethyl silyl ether

Base Information

• Chemical Name: (1R,2S)-trans-2-hydroxy-1-cyanocyclohexane trimethyl silyl ether
• CAS No.: 182698-20-0
• Molecular Formula: C₁₀H₁₉NOSi
• Molecular Weight: 197.352
• Mol file: 182698-20-0.mol

Synonyms:(1R,2S)-trans-2-hydroxy-1-cyanocyclohexane trimethyl silyl ether

Chemical Property of (1R,2S)-trans-2-hydroxy-1-cyanocyclohexane trimethyl silyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-trans-2-hydroxy-1-cyanocyclohexane trimethyl silyl ether

There total 9 articles about (1R,2S)-trans-2-hydroxy-1-cyanocyclohexane trimethyl silyl ether 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:

cyclohexene oxide (286-20-4) + trimethylsilyl cyanide (7677-24-9) → (1S,2R)-trans-2-hydroxy-1-cyanocyclohexane trimethylsilyl ether (265096-49-9) + (1R,2S)-trans-2-hydroxy-1-cyanocyclohexane trimethyl silyl ether (182698-20-0)

Guidance literature:

With C₇₆H₁₁₂N₄O₂Ti₂; In dichloromethane; at 25 ℃; for 24h; optical yield given as %ee; Inert atmosphere;

DOI:10.1002/adsc.200900523

Reference yield:

cyclohexene oxide (286-20-4) + trimethylsilyl cyanide (7677-24-9) → (1S,2R)-trans-2-hydroxy-1-cyanocyclohexane trimethylsilyl ether (265096-49-9) + (1R,2S)-trans-2-hydroxy-1-cyanocyclohexane trimethyl silyl ether (182698-20-0) + (1R,2R)-(2-isocyanocyclohexyloxy)trimethylsilane

Guidance literature:

cyclohexene oxide; With titanium(IV) isopropylate; C₄₈H₄₆N₄O₄; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

trimethylsilyl cyanide; In dichloromethane; at 20 ℃; for 24h; Overall yield = 20 %; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.04.012

Reference yield:

trimethylsilyl cyanide (7677-24-9) + cyclohexane-1,2-epoxide (286-20-4) → (1S,2R)-trans-2-hydroxy-1-cyanocyclohexane trimethylsilyl ether (265096-49-9) + (1R,2S)-trans-2-hydroxy-1-cyanocyclohexane trimethyl silyl ether (182698-20-0)

Guidance literature:

titanium(IV) isopropylate; 3-F-2-HO-C₆H₃-CH=t-Leu-Thr(t-Bu)-OMe Schiff base; In dichloromethane; at 4 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

upstream raw materials:

trimethylsilyl cyanide

cyclohexane-1,2-epoxide

cyclohexene oxide

chloro-trimethyl-silane

Downstream raw materials:

(1R,2S)-2-hydroxycyclohexane-1-carbonitrile

Refernces

• 1、 Saha, Biswajit,Lin, Mei-Huey,RajanBabu. "Exceptionally active yttrium-salen complexes for the catalyzed ring opening of epoxides by TMSCN and TMSN3". . p. 8648 - 8655. Retrieved 2007.
• 2、 Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Rebolledo, Francisca. "Developing a Biocascade Process: Concurrent Ketone Reduction-Nitrile Hydrolysis of 2-Oxocycloalkanecarbonitriles". supporting information. p. 3366 - 3369. Retrieved 2016/07/26.
• 3、 Belokon, Yuri N.,Chusov, Denis,Peregudov, Alexander S.,Yashkina, Lidia V.,Timofeeva, Galina I.,Maleev, Victor I.,North, Michael,Kagan, Henri B.. "Asymmetric meso-epoxide ring-opening with trimethylsilyl cyanide promoted by chiral binuclear complexes of titanium. Dichotomy of C-C versus C-N bond formation". scheme or table. p. 3157 - 3167. Retrieved 2010/07/03.