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

Base Information

• Chemical Name: ethyl (1R,2S)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-3-oxocyclohex-4-ene-1-carboxylate
• CAS No.: 173396-47-9
• Molecular Formula: C₁₇H₂₄O₆Si
• Molecular Weight: 352.459
• Mol file: 173396-47-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about ethyl (1R,2S)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-3-oxocyclohex-4-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: 95.0%

ethyl (1R,2S,3R,5S)-2,3-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate (173396-45-7) → ethyl (1R,2S)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-3-oxocyclohex-4-ene-1-carboxylate (173396-47-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide;

DOI:10.1039/c39950002519

Reference yield:

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

Guidance literature:

Multi-step reaction with 3 steps

1: 47 percent / N,N'-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 16 h / 20 °C

2: 92 percent / K₂CO₃ / ethanol / 1 h / 0 °C

3: 90 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

With dmap; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In ethanol; dichloromethane; 3: Swern oxidation;

DOI:10.1039/b508675b

Reference yield:

ethyl (1R,2S,3R,5S)-3-[(S)-O-(chloroacetyl)mandeloyloxy]-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate (173289-84-4) → ethyl (1R,2S)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-3-oxocyclohex-4-ene-1-carboxylate (173396-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / K₂CO₃ / ethanol / 1 h / 0 °C

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

With oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; In ethanol; dichloromethane; 2: Swern oxidation;

DOI:10.1039/b508675b

upstream raw materials:

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

ethyl (1R,2S,3S,5S)-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate

ethyl (1R,2S,3S,4R,5S)-2,4-dihydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

Downstream raw materials:

C₅₂H₉₄O₁₁Si₃

C₄₁H₆₈O₁₁Si

(1R,2S,3R,4R)-2-[(5R,1Z,3E,7E)-1-carbomethoxy-5,7-dimethyl-9-{(2R,3S,6R,8R,10S)-10-hydroxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}nona-1,3,7-trien-1-yl]-2,3-dihydroxy-4-methoxy-5-methylcyclohex-5-ene-1-carboxylic acid

(6R)-6-hydroxymilbemycin E