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

Base Information

• Chemical Name: ethyl (1RS,2SR,3SR,4RS,5SR)-3-benzyloxy-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate
• CAS No.: 135352-18-0
• Molecular Formula: C₂₄H₃₄O₆Si
• Molecular Weight: 446.616
• Mol file: 135352-18-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about ethyl (1RS,2SR,3SR,4RS,5SR)-3-benzyloxy-2,4-dihydroxy-5-methyl-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: 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:

Benzyloxymethyl isopropenyl ketone (103791-04-4) → 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:

Multi-step reaction with 2 steps

1: 50 percent / aq. NaOH / ethanol / 20 h / 20 °C

2: 84 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / 96 h / 20 °C

With sodium hydroxide; acetic acid; tetramethylammonium triacetoxyborohydride; In ethanol; acetonitrile; 1: Robinson reaction;

DOI:10.1039/b508670a

Reference yield:

ethyl 3-oxo-3-(2'-trimethylsilyl-3'-furyl)propanoate (114047-82-4) → 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:

Multi-step reaction with 2 steps

1: 50 percent / aq. NaOH / ethanol / 20 h / 20 °C

2: 84 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / 96 h / 20 °C

With sodium hydroxide; acetic acid; tetramethylammonium triacetoxyborohydride; In ethanol; acetonitrile; 1: Robinson reaction;

DOI:10.1039/b508670a

upstream raw materials:

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

Benzyloxymethyl isopropenyl ketone

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

Downstream raw materials:

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

6β-Hydroxy-3,4-dihydromilbemycin E

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