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

Base Information

Chemical Name:ethyl (1R,2S,3R,4R)-2,3-dihydroxy-4-methoxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate
CAS No.:173396-52-6
Molecular Formula:C₁₈H₂₈O₆Si
Molecular Weight:368.502
Hs Code.:

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

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

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

There total 14 articles about ethyl (1R,2S,3R,4R)-2,3-dihydroxy-4-methoxy-5-methyl-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: 93.0%

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

: 74-88-4
methyl iodide

: 173396-52-6
ethyl (1R,2S,3R,4R)-2,3-dihydroxy-4-methoxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

Guidance literature:: ethyl (1R,2S,3R,4R)-5-methyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate; With di(n-butyl)tin oxide; In methanol; for 24h; Heating;

methyl iodide; With tetra-(n-butyl)ammonium iodide; In benzene; for 36h; Heating;
DOI:10.1039/b508675b

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

: 173396-52-6
ethyl (1R,2S,3R,4R)-2,3-dihydroxy-4-methoxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: t-BuOOH / CH₂Cl₂ / 3 h / 20 °C

2.1: n-Bu₂SnO / methanol / 24 h / Heating

2.2: 93 percent / tetra-n-butylammonium iodide / benzene / 36 h / Heating

With tert.-butylhydroperoxide; di(n-butyl)tin oxide; In methanol; dichloromethane;
DOI:10.1039/b508675b

Reference yield:

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

: 173396-52-6
ethyl (1R,2S,3R,4R)-2,3-dihydroxy-4-methoxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / pyridine / tetrahydrofuran / 0.08 h

2.1: 75 percent / NMe₄BH(OAc)3; AcOH / acetonitrile / 1 h / 20 °C

3.1: t-BuOOH / CH₂Cl₂ / 3 h / 20 °C

4.1: n-Bu₂SnO / methanol / 24 h / Heating

4.2: 93 percent / tetra-n-butylammonium iodide / benzene / 36 h / Heating

With pyridine; tert.-butylhydroperoxide; di(n-butyl)tin oxide; acetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1039/b508675b