[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (7R,Z)-7-nitromethyl-2-(triisopropylsilyloxy)cyclohept-1-ene-1-carboxylate

Base Information

Chemical Name:[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (7R,Z)-7-nitromethyl-2-(triisopropylsilyloxy)cyclohept-1-ene-1-carboxylate
CAS No.:1146352-89-7
Molecular Formula:C₃₄H₅₅NO₅Si
Molecular Weight:585.9
Hs Code.:

Synonyms:[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (7R,Z)-7-nitromethyl-2-(triisopropylsilyloxy)cyclohept-1-ene-1-carboxylate

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Chemical Property of [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (7R,Z)-7-nitromethyl-2-(triisopropylsilyloxy)cyclohept-1-ene-1-carboxylate

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Technology Process of [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (7R,Z)-7-nitromethyl-2-(triisopropylsilyloxy)cyclohept-1-ene-1-carboxylate

There total 5 articles about [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (7R,Z)-7-nitromethyl-2-(triisopropylsilyloxy)cyclohept-1-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: 63.0%

: 75-52-5
nitromethane

: 1146352-87-5
[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl] 7-oxocyclohept-1-enecarboxylate

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 1146352-89-7
[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (7R,Z)-7-nitromethyl-2-(triisopropylsilyloxy)cyclohept-1-ene-1-carboxylate

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 9h; Inert atmosphere;
DOI:10.1021/acs.orglett.8b01087

Reference yield: 63.0%

: 75-52-5
nitromethane

: 1146352-87-5
[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl] 7-oxocyclohept-1-enecarboxylate

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 1146352-92-2
[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl] (2R)-2-nitromethyl-7-oxocycloheptanecarboxylate

: 1146352-89-7
[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (7R,Z)-7-nitromethyl-2-(triisopropylsilyloxy)cyclohept-1-ene-1-carboxylate

Guidance literature:: nitromethane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.366667h; Inert atmosphere;

[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl] 7-oxocyclohept-1-enecarboxylate; In tetrahydrofuran; hexane; at -78 ℃; for 1.83333h; Inert atmosphere;

triisopropylsilyl trifluoromethanesulfonate; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at -78 - -10 ℃; Inert atmosphere;
DOI:10.1021/ol9003405

Reference yield:

: 65253-04-5
(-)-8-phenylmenthol

: 1146352-89-7
[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (7R,Z)-7-nitromethyl-2-(triisopropylsilyloxy)cyclohept-1-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / mineral oil; benzene / 7 h / Inert atmosphere; Reflux

1.2: 96 h / Inert atmosphere; Reflux

2.1: lithium hexamethyldisilazane; C₁₁H₁₄ClNS / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran / 9 h / -78 - 0 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium hydride; C₁₁H₁₄ClNS; lithium hexamethyldisilazane; In tetrahydrofuran; mineral oil; benzene;
DOI:10.1021/acs.orglett.8b01087