Ethyl (1S,2R,4R,5R)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate

Base Information

• Chemical Name: Ethyl (1S,2R,4R,5R)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate
• CAS No.: 188472-58-4
• Molecular Formula: C₁₇H₂₈O₅Si
• Molecular Weight: 340.492

Synonyms:Ethyl (1S,2R,4R,5R)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate

Chemical Property of Ethyl (1S,2R,4R,5R)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate

Chemical Property:

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Technology Process of Ethyl (1S,2R,4R,5R)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate

There total 4 articles about Ethyl (1S,2R,4R,5R)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate 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%

Ethyl (1S,2R,4R,5R)-4-<(2S)-2-acetoxy-2-phenylacetoxy>-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate (129312-18-1) → Ethyl (1S,2R,4R,5R)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate (188472-58-4)

Guidance literature:

With potassium carbonate; In ethanol; for 16h; Ambient temperature;

DOI:10.1039/a605894i

Reference yield: 7.0%

(S)-acetylmandelic acid (7322-88-5) + (1RS,2SR,5SR)-ethyl 2,4-dihydroxy-5-methyl-2-(2'-trimethylsilyl-3'-furyl)cyclohexanecarboxylate → Ethyl (1S,2R,4R,5R)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate (188472-58-4) + Ethyl (1R,2S,4S,5S)-2-hydroxy-4-<(2S)-2-hydroxy-2-phenylacetoxy>-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate (129313-41-3) + Ethyl (1S,2R,4R,5R)-2-hydroxy-4-<(2S)-2-hydroxy-2-phenylacetoxy>-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate

Guidance literature:

With dmap; potassium carbonate; dicyclohexyl-carbodiimide; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, r.t., 16 h, 2.) EtOH, 0 deg C, 2 h;

DOI:10.1039/a605894i

Reference yield:

(1RS,2SR,5SR)-ethyl 2-hydroxy-5-methyl-4-oxo-2-(2'-trimethylsilyl-3'-furyl)cyclohexanecarboxylate → Ethyl (1R,2S,4S,5S)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate (129312-19-2) + Ethyl (1S,2R,4R,5R)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate (188472-58-4)

Guidance literature:

With sodium tris(acetoxy)borohydride; In acetic acid; Yield given;

DOI:10.1039/c39890001250

upstream raw materials:

(S)-acetylmandelic acid

Ethyl (1S,2R,4R,5R)-4-<(2S)-2-acetoxy-2-phenylacetoxy>-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexanecarboxylate

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