2-trimethylsilylethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

Base Information

Chemical Name:2-trimethylsilylethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate
CAS No.:173289-88-8
Molecular Formula:C₂₇H₅₀O₇Si₃
Molecular Weight:570.946
Hs Code.:

2-trimethylsilylethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

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

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

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

There total 18 articles about 2-trimethylsilylethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-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: 82.0%

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 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

: 173289-88-8
2-trimethylsilylethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

Guidance literature:: DOI:10.1039/c39950002519

Reference yield:

: 173396-48-0
ethyl (1R,2S,5R)-2-hydroxy-5-methyl-5-phenylselanyl-2-(2-trimethylsilyl-3-furyl)-3,4-dioxocyclohexane-1-carboxylate

: 173289-88-8
2-trimethylsilylethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 75 percent / NMe₄BH(OAc)3; AcOH / acetonitrile / 1 h / 20 °C

2.1: t-BuOOH / CH₂Cl₂ / 3 h / 20 °C

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

3.2: 93 percent / tetra-n-butylammonium iodide / benzene / 36 h / Heating

4.1: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

5.1: 391 mg / aq. NaOH / ethanol / 24 h / 0 °C

6.1: 390 mg / N,N'-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 18 h / 20 °C

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

Reference yield:

: 173396-45-7
ethyl (1R,2S,3R,5S)-2,3-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate

: 173289-88-8
2-trimethylsilylethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 90 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 88 percent / pyridine / tetrahydrofuran / 0.08 h

3.1: 75 percent / NMe₄BH(OAc)3; AcOH / acetonitrile / 1 h / 20 °C

4.1: t-BuOOH / CH₂Cl₂ / 3 h / 20 °C

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

5.2: 93 percent / tetra-n-butylammonium iodide / benzene / 36 h / Heating

6.1: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

7.1: 391 mg / aq. NaOH / ethanol / 24 h / 0 °C

8.1: 390 mg / N,N'-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 18 h / 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; sodium hydroxide; oxalyl dichloride; di(n-butyl)tin oxide; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile; 1.1: Swern oxidation;
DOI:10.1039/b508675b