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

Base Information

Chemical Name: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
CAS No.:135352-21-5
Molecular Formula:C₂₇H₅₂O₇Si₃
Molecular Weight:572.962
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 22 articles about 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 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: 93.0%

: 2-trimethylsilylethyl (1RS,2SR,3RS,4RS,5SR)-2,4-dihydroxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate

: 74-88-4
methyl iodide

: 135352-21-5
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

Guidance literature:: With cetyltrimethylammonim bromide; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at 0 ℃; for 0.25h;
DOI:10.1039/b508670a

Reference yield: 80.0%

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

: (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylic acid

: 135352-21-5
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

Guidance literature:: With dmap; dicyclohexyl-carbodiimide;
DOI:10.1016/S0040-4039(00)79699-7

Reference yield:

: 135352-16-8
ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate

: 135352-21-5
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

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