(1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-enoic acid

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Chemical Name:(1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-enoic acid
CAS No.:173289-90-2
Molecular Formula:C₂₂H₃₈O₇Si₂
Molecular Weight:470.711
Hs Code.:

Synonyms:(1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-enoic acid

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Chemical Property of (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-enoic acid

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Technology Process of (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-enoic acid

There total 17 articles about (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-enoic acid 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: 97.0%

: 173289-89-9
ethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

: 173289-90-2
(1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-enoic acid

Guidance literature:: With sodium hydroxide;
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

: 173289-90-2
(1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-enoic acid

Guidance literature:: Multi-step reaction with 4 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

3.1: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

4.1: 391 mg / aq. NaOH / ethanol / 24 h / 0 °C

With tert.-butylhydroperoxide; sodium hydroxide; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; 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

: 173289-90-2
(1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-enoic acid

Guidance literature:: Multi-step reaction with 6 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

5.1: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

6.1: 391 mg / aq. NaOH / ethanol / 24 h / 0 °C

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