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

Base Information

Chemical Name:ethyl (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate
CAS No.:135352-20-4
Molecular Formula:C₂₄H₄₄O₇Si₂
Molecular Weight:500.78
Hs Code.:

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

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

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

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

There total 10 articles about ethyl (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohexane-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: 62.0%

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

: 74-88-4
methyl iodide

: 135352-20-4
ethyl (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

Guidance literature:: With silver(l) oxide;
DOI:10.1016/S0040-4039(00)79699-7

Reference yield:

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

: 135352-20-4
ethyl (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / H₂ / Pd/C / ethanol

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

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

4: 91 percent / i-Pr₂NEt / CH₂Cl₂ / 16 h / 20 °C

5: 70 percent / K₂CO₃ / ethanol / 48 h / 20 °C

6: 62 percent / Ag₂O / 48 h / Heating

With oxalyl dichloride; hydrogen; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile; 2: Swern oxidation;
DOI:10.1039/b508670a

Reference yield:

: 135352-18-0
ethyl (1RS,2SR,3SR,4RS,5SR)-3-benzyloxy-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

: 135352-20-4
ethyl (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / DMAP; dicyclohexylcarbodiimide / CH₂Cl₂ / 16 h / 20 °C

2: 91 percent / H₂ / Pd/C / ethanol

3: 100 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -50 - 20 °C

4: 99 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / 16 h

5: 91 percent / i-Pr₂NEt / CH₂Cl₂ / 16 h / 20 °C

6: 70 percent / K₂CO₃ / ethanol / 48 h / 20 °C

7: 62 percent / Ag₂O / 48 h / Heating

With dmap; 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; 3: Swern oxidation;
DOI:10.1039/b508670a