3(R^*)-acetoxy-4(R^*)-<5-(5-methyl-1,3-cyclopentadienyl)>-4(R^*)-<<(tert-butyldimethylsilyl)oxy>methyl>methylenecyclohexane

Base Information

• Chemical Name: 3(R^*)-acetoxy-4(R^*)-<5-(5-methyl-1,3-cyclopentadienyl)>-4(R^*)-<<(tert-butyldimethylsilyl)oxy>methyl>methylenecyclohexane
• CAS No.: 125475-54-9
• Molecular Formula: C₂₂H₃₆O₃Si
• Molecular Weight: 376.612

Synonyms:3(R^*)-acetoxy-4(R^*)-<5-(5-methyl-1,3-cyclopentadienyl)>-4(R^*)-<<(tert-butyldimethylsilyl)oxy>methyl>methylenecyclohexane

Chemical Property of 3(R^*)-acetoxy-4(R^*)-<5-(5-methyl-1,3-cyclopentadienyl)>-4(R^*)-<<(tert-butyldimethylsilyl)oxy>methyl>methylenecyclohexane

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of 3(R^*)-acetoxy-4(R^*)-<5-(5-methyl-1,3-cyclopentadienyl)>-4(R^*)-<<(tert-butyldimethylsilyl)oxy>methyl>methylenecyclohexane

There total 13 articles about 3(R^*)-acetoxy-4(R^*)-<5-(5-methyl-1,3-cyclopentadienyl)>-4(R^*)-<<(tert-butyldimethylsilyl)oxy>methyl>methylenecyclohexane 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:

(1-Methylcyclopent-2-enyl)essigsaeure-methylester (90511-20-9) → 3(R*)-acetoxy-4(R*)-<5-(5-methyl-1,3-cyclopentadienyl)>-4(R*)-<<(tert-butyldimethylsilyl)oxy>methyl>methylenecyclohexane (125475-54-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) LDA / 1.) THF, -78 deg C, 1.5 h, 2.) -78 deg C, 45 min

2: N-bromosuccinimide, AIBN / CCl₄ / 0.33 h / Heating

3: calcium carbonate / dimethylformamide / 4 h / 90 °C

4: 1.) NaH / 1.) THF, reflux, 1.5 h, 2.) reflux, 16 h

5: 98 percent / aq. HF / acetonitrile / 1 h / Ambient temperature

6: tri-n-butyl phosphine / tetrahydrofuran / 0.75 h

7: 30percent aq. hydrogen peroxide / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) RT, 3 h

8: 88 percent / LiAlH₄ / diethyl ether / 1.) 0 deg C, 1 h, 2.) 25 deg C, 1 h

9: 78 percent / oxalyl chloride, DMSO, triethylamine / CH₂Cl₂ / -78 - 20 °C

10: Eu(fod)3, molecular sives (4 Angstroem) / CH₂Cl₂ / 120 h / Ambient temperature

11: 52 percent / diazabicyclo<5.4.0>undec-7-ene / benzene / 12 h

12: lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 1 h / Ambient temperature

13: Et₃N / CH₂Cl₂ / 8 h / Ambient temperature

With N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; lithium tri(t-butoxy)aluminum hydride; 2,2'-azobis(isobutyronitrile); tributylphosphine; molecular sives (4 Angstroem); hydrogen fluoride; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; calcium carbonate; lithium diisopropyl amide; Eu(fod)3; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

Reference yield:

2-Hydroxy-1-(1-methyl-cyclopenta-2,4-dienyl)-4-methylene-cyclohexanecarbaldehyde (125475-15-2,125475-27-6) → 3(R*)-acetoxy-4(R*)-<5-(5-methyl-1,3-cyclopentadienyl)>-4(R*)-<<(tert-butyldimethylsilyl)oxy>methyl>methylenecyclohexane (125475-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 52 percent / diazabicyclo<5.4.0>undec-7-ene / benzene / 12 h

2: lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 1 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 8 h / Ambient temperature

With lithium tri(t-butoxy)aluminum hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; benzene;

Reference yield:

2-(3-methyl-3-butenyl)-2-<5-(5-methyl-1,3-cyclopentadienyl)>malondialdehyde (125475-16-3) → 3(R*)-acetoxy-4(R*)-<5-(5-methyl-1,3-cyclopentadienyl)>-4(R*)-<<(tert-butyldimethylsilyl)oxy>methyl>methylenecyclohexane (125475-54-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Eu(fod)3, molecular sives (4 Angstroem) / CH₂Cl₂ / 120 h / Ambient temperature

2: 52 percent / diazabicyclo<5.4.0>undec-7-ene / benzene / 12 h

3: lithium tri-tert-butoxyaluminum hydride / tetrahydrofuran / 1 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 8 h / Ambient temperature

With lithium tri(t-butoxy)aluminum hydride; molecular sives (4 Angstroem); 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; Eu(fod)3; In tetrahydrofuran; dichloromethane; benzene;

upstream raw materials:

t-butyldimethylsiyl triflate

Acetic acid (1S,2S)-2-hydroxymethyl-2-(1-methyl-cyclopenta-2,4-dienyl)-5-methylene-cyclohexyl ester

(1-Methylcyclopent-2-enyl)essigsaeure-methylester

2-Hydroxy-1-(1-methyl-cyclopenta-2,4-dienyl)-4-methylene-cyclohexanecarbaldehyde

Downstream raw materials:

4(R^*)-<<(tert-butyldimethylsilyl)oxy>methyl>-4(R^*)-<4-<3(R^*),5(S^*)-dihydroxy-4(r)-methyl-1-cyclopentenyl>>-3(R^*)-hydroxymethylenecyclohexane

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