ethyl (1R,2S,3R,4R)-5-methyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

Base Information

Chemical Name:ethyl (1R,2S,3R,4R)-5-methyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate
CAS No.:173396-50-4
Molecular Formula:C₁₇H₂₆O₆Si
Molecular Weight:354.475
Hs Code.:

Synonyms:ethyl (1R,2S,3R,4R)-5-methyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

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Chemical Property of ethyl (1R,2S,3R,4R)-5-methyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

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Technology Process of ethyl (1R,2S,3R,4R)-5-methyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

There total 14 articles about ethyl (1R,2S,3R,4R)-5-methyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate 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:

: 173289-85-5
ethyl (1R,2S,3R,4S,5R)-2,3-dihydroxy-5-methyl-5-phenylselanyl-4-trichloroacetoxy-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

: 173396-50-4
ethyl (1R,2S,3R,4R)-5-methyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

: ethyl (1R,2S,3R,4R)-5-methylene-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

Guidance literature:: With tert.-butylhydroperoxide; dmap; ethanol; Yield given. Multistep reaction; 1.) benzene;
DOI:10.1039/c39950002519

Reference yield:

: 173396-49-1
ethyl (1R,2S,3R,4S,5R)-5-methyl-5-phenylselanyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)-cyclohexane-1-carboxylate

: 173396-50-4
ethyl (1R,2S,3R,4R)-5-methyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

: ethyl (1R,2S,3R,4R)-5-methylene-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

Guidance literature:: With tert.-butylhydroperoxide; In dichloromethane; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1039/c39950002519

Reference yield:

: 173396-47-9
ethyl (1R,2S)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-3-oxocyclohex-4-ene-1-carboxylate

: 173396-50-4
ethyl (1R,2S,3R,4R)-5-methyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / pyridine / tetrahydrofuran / 0.08 h

2: 75 percent / NMe₄BH(OAc)3; AcOH / acetonitrile / 1 h / 20 °C

3: t-BuOOH / CH₂Cl₂ / 3 h / 20 °C

With pyridine; tert.-butylhydroperoxide; acetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1039/b508675b