ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate

Base Information

• Chemical Name: ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate
• CAS No.: 135352-16-8
• Molecular Formula: C₂₄H₃₂O₆Si
• Molecular Weight: 444.6
• Mol file: 135352-16-8.mol

Synonyms:ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate

Chemical Property of ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate

There total 1 articles about ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-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: 50.0%

Benzyloxymethyl isopropenyl ketone (103791-04-4) + ethyl 3-oxo-3-(2'-trimethylsilyl-3'-furyl)propanoate (114047-82-4) → ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate (135352-16-8)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃;

DOI:10.1016/S0040-4039(00)79699-7

Reference yield: 84.0%

ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate (135352-16-8) → ethyl (1RS,2SR,3SR,4RS,5SR)-3-benzyloxy-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate (135352-18-0)

Guidance literature:

With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile;

DOI:10.1016/S0040-4039(00)79699-7

Reference yield:

ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate (135352-16-8) → 2-trimethylsilylethyl (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate (135352-21-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 84 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / 96 h / 20 °C

2: 85 percent / DMAP; dicyclohexylcarbodiimide / CH₂Cl₂ / 16 h / 20 °C

3: 91 percent / H₂ / Pd/C / ethanol

4: 100 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -50 - 20 °C

5: 99 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / 16 h

6: 91 percent / i-Pr₂NEt / CH₂Cl₂ / 16 h / 20 °C

7: 70 percent / K₂CO₃ / ethanol / 48 h / 20 °C

8: 62 percent / Ag₂O / 48 h / Heating

9: 99 percent / aq. NaOH / ethanol / 48 h / 20 °C

10: 80 percent / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 16 h / 20 °C

With dmap; sodium hydroxide; oxalyl dichloride; hydrogen; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; silver(l) oxide; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile; 4: Swern oxidation;

DOI:10.1039/b508670a

upstream raw materials:

Benzyloxymethyl isopropenyl ketone

ethyl 3-oxo-3-(2'-trimethylsilyl-3'-furyl)propanoate

Downstream raw materials:

ethyl (1RS,2SR,3SR,4RS,5SR)-3-benzyloxy-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

ethyl (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate