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

Base Information

• Chemical Name: 4(R^*)-<<(tert-butyldimethylsilyl)oxy>methyl>-4(R^*)-<4-<3(R^*),5(S^*)-dihydroxy-4(r)-methyl-1-cyclopentenyl>>-3(R^*)-hydroxymethylenecyclohexane
• CAS No.: 125475-53-8
• Molecular Formula: C₂₀H₃₆O₄Si
• Molecular Weight: 368.589

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 4(R^*)-<<(tert-butyldimethylsilyl)oxy>methyl>-4(R^*)-<4-<3(R^*),5(S^*)-dihydroxy-4(r)-methyl-1-cyclopentenyl>>-3(R^*)-hydroxymethylenecyclohexane

There total 15 articles about 4(R^*)-<<(tert-butyldimethylsilyl)oxy>methyl>-4(R^*)-<4-<3(R^*),5(S^*)-dihydroxy-4(r)-methyl-1-cyclopentenyl>>-3(R^*)-hydroxymethylenecyclohexane 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:

t-butyldimethylsiyl triflate (69739-34-0) → 4(R*)-<<(tert-butyldimethylsilyl)oxy>methyl>-4(R*)-<4-<3(R*),5(S*)-dihydroxy-4(r)-methyl-1-cyclopentenyl>>-3(R*)-hydroxymethylenecyclohexane (125475-53-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 8 h / Ambient temperature

2: 1.) O₂, tetraphenylporphine, 2.) LiAlH₄ / 1.) in CS₂, -78 deg C, 5 h, irradiation, 2.) ether, -78 deg C, 1.5 h

With lithium aluminium tetrahydride; oxygen; 5,15,10,20-tetraphenylporphyrin; triethylamine; In dichloromethane;

Reference yield:

(1-Methylcyclopent-2-enyl)essigsaeure-methylester (90511-20-9) → 4(R*)-<<(tert-butyldimethylsilyl)oxy>methyl>-4(R*)-<4-<3(R*),5(S*)-dihydroxy-4(r)-methyl-1-cyclopentenyl>>-3(R*)-hydroxymethylenecyclohexane (125475-53-8)

Guidance literature:

Multi-step reaction with 14 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

14: 1.) O₂, tetraphenylporphine, 2.) LiAlH₄ / 1.) in CS₂, -78 deg C, 5 h, irradiation, 2.) ether, -78 deg C, 1.5 h

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; oxygen; 5,15,10,20-tetraphenylporphyrin; 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) → 4(R*)-<<(tert-butyldimethylsilyl)oxy>methyl>-4(R*)-<4-<3(R*),5(S*)-dihydroxy-4(r)-methyl-1-cyclopentenyl>>-3(R*)-hydroxymethylenecyclohexane (125475-53-8)

Guidance literature:

Multi-step reaction with 4 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

4: 1.) O₂, tetraphenylporphine, 2.) LiAlH₄ / 1.) in CS₂, -78 deg C, 5 h, irradiation, 2.) ether, -78 deg C, 1.5 h

With lithium aluminium tetrahydride; lithium tri(t-butoxy)aluminum hydride; oxygen; 5,15,10,20-tetraphenylporphyrin; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; benzene;

upstream raw materials:

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

t-butyldimethylsiyl triflate

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

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

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