<5R^*,6S^*>-3-methoxy-2,5,6-trimethyl-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one

Base Information

• Chemical Name: <5R^*,6S^*>-3-methoxy-2,5,6-trimethyl-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one
• CAS No.: 111470-84-9
• Molecular Formula: C₁₈H₃₂O₂Si
• Molecular Weight: 308.536

Synonyms:<5R^*,6S^*>-3-methoxy-2,5,6-trimethyl-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one

Chemical Property of <5R^*,6S^*>-3-methoxy-2,5,6-trimethyl-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one

Chemical Property:

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Technology Process of <5R^*,6S^*>-3-methoxy-2,5,6-trimethyl-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one

There total 6 articles about <5R^*,6S^*>-3-methoxy-2,5,6-trimethyl-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one 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:

(E)-2-methyl-2-buten-1-ol (497-02-9) → <5R*,6S*>-3-methoxy-2,5,6-trimethyl-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one (111470-84-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-butyllithium, tetramethylethylenediamine / 1a.) ether, 0 deg C, 30 min, 1b.) ether/THF, RT, 48 h, 2a.) -45 deg C, 10 min, 2b.) RT, 20 min

2: 93 percent / aq. 1N H₂SO₄ / tetrahydrofuran / 0.5 h / Ambient temperature

3: triethylamine / tetrahydrofuran / 4 h / 0 °C

4: sodium iodide / acetone / 2 h / 0 °C

5: 1.) lithium diisopropylamide, HMPA / 1.) THF/hexane, -78 deg C, 30 min, 2a.) -78 deg C, 30 min 2b.) from -78 deg C to RT, 12 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; triethylamine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; acetone;

DOI:10.1021/jo00236a013

Reference yield:

Methanesulfonic acid (Z)-2-trimethylsilanylmethyl-but-2-enyl ester → <5R*,6S*>-3-methoxy-2,5,6-trimethyl-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one (111470-84-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium iodide / acetone / 2 h / 0 °C

2: 1.) lithium diisopropylamide, HMPA / 1.) THF/hexane, -78 deg C, 30 min, 2a.) -78 deg C, 30 min 2b.) from -78 deg C to RT, 12 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium iodide; lithium diisopropyl amide; In acetone;

DOI:10.1021/jo00236a013

Reference yield:

(Z)-2-<(trimethylsilyl)methyl>-but-2-ene-1-ol (100641-08-5) → <5R*,6S*>-3-methoxy-2,5,6-trimethyl-6-<2-<(trimethylsilyl)methyl>-2-butenyl>-2-cyclohexen-1-one (111470-84-9)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 4 h / 0 °C

2: sodium iodide / acetone / 2 h / 0 °C

3: 1.) lithium diisopropylamide, HMPA / 1.) THF/hexane, -78 deg C, 30 min, 2a.) -78 deg C, 30 min 2b.) from -78 deg C to RT, 12 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; triethylamine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; acetone;

DOI:10.1021/jo00236a013

upstream raw materials:

(Z)-2-<(trimethylsilyl)methyl>-2-buten-1-yl iodide

3-Methoxy-2,5,6-trimethyl-cyclohex-2-enone

<5R^*>-3-methoxy-2,5-dimethyl-2-cyclohexen-1-one

(E)-2-methyl-2-buten-1-ol

Downstream raw materials:

<4R^*,5S^*>-2,4,5-trimethyl-4-<2-<(trimethylsilyl)methyl>-2-butenyl>-3-vinyl-2-cyclohexen-1-one

(+/-)-guadalupol benzoate

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