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146436-22-8

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Basic Information
CAS No.: 146436-22-8
Name: terpestacin
Article Data: 7
Molecular Structure:
Molecular Structure of 146436-22-8 (terpestacin)
Formula: C25H38 O4
Molecular Weight: 402.574
Synonyms: 1(3aH)-Cyclopentacyclopentadecenone,4,7,8,9,12,13,16,16a-octahydro-2,7-dihydroxy-3-(2-hydroxy-1-methylethyl)-6,10,14,16a-tetramethyl-,[3aR-[3(S*),3aR*,5E,7S*,10E,14E,16aS*]]-; (-)-Terpestacin;(1S,11S,15R,23S)-Terpestacin; BU 4641V; Deacetylfusaproliferin; Siccanol;Terpestacin
Density: 1.064g/cm3
Boiling Point: 580.5°Cat760mmHg
Flash Point: 318.9°C
PSA: 77.76000
LogP: 5.18610
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(5E,10E,14E)-(3aR,7S,16aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3-((S)-2-hydroxy-1-methyl-ethyl)-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran94%
1385030-65-8

C37H66O4Si2

146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
With hydrogen fluoride In tetrahydrofuran; water at 20℃; for 3h;90%
935263-74-4

7-hydroxy-3-(2-hydroxy-1-methyl-ethyl)-2-(4-methoxy-benzyloxy)-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydro-3aH-cyclopentacyclopentadecen-1-one

146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
With dimethylsulfide; magnesium bromide In dichloromethane at 20℃; for 0.666667h;74%
With dimethylsulfide; magnesium bromide ethyl etherate In dichloromethane at -78 - 20℃; Inert atmosphere;74%

C39H46O6

146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 50℃; for 1h; Hydrolysis; deprotection;70%

(3E,7E,12E)-(1S,11S,15R,17S)-11,20-Dihydroxy-1,4,8,12,17-pentamethyl-19-oxa-tricyclo[13.6.0.016,20]henicosa-3,7,12-trien-21-one

146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 2h;2.5 mg
935263-58-4

8-benzenesulfonyl-2,6-dimethyl-octa-1,6-dien-3-ol

146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
2: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
3: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
4: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
5: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
6: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
7: Cs2CO3; Bu4NI / dimethylformamide / 2 h
8: 8.7 mg / pyridine / 3 h / 20 °C
9: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
10: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
11: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
12: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
13: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
935263-72-2

[3-(5-benzenesulfonyl-3-methyl-pent-3-enyl)-2-methyl-oxiranyl]-methanol

146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: pyridine; iodine; PPh3 / acetonitrile; diethyl ether / 2 h / 0 °C
1.2: 74 percent / water / acetonitrile; diethyl ether / 8 h / 38 °C
2.1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
3.1: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
4.1: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
5.1: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
6.1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
7.1: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
8.1: Cs2CO3; Bu4NI / dimethylformamide / 2 h
9.1: 8.7 mg / pyridine / 3 h / 20 °C
10.1: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
11.1: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
12.1: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
13.1: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
14.1: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
935263-61-9

5-methyl-5-(3-methyl-4-triisopropylsilanyloxy-but-2-enyl)-cyclopent-3-ene-1,2-dione

146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1: MgBr2*Et2O / CH2Cl2 / 1 h / 20 °C
2: 79 percent / Cs2CO3; Bu4NI / dimethylformamide / 2.5 h / 20 °C
3: 84 percent / TBAF*3H2O / tetrahydrofuran / 2 h / 0 °C
4: 88 percent / PPh3; CBr4 / acetonitrile / 20 °C
5: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
6: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
7: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
8: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
9: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
10: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
11: Cs2CO3; Bu4NI / dimethylformamide / 2 h
12: 8.7 mg / pyridine / 3 h / 20 °C
13: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
14: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
15: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
16: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
17: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme

3-methyl-2-(1-methyl-1-triisopropylsilanyloxymethyl-allyloxy)-cyclopent-2-enone

146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: CHCl3 / 0.5 h / 100 - 120 °C / microwave irradiation
1.2: Cs2CO3 / Pd(OAc)2 / acetonitrile / 0.5 h / 20 °C
2.1: MgBr2*Et2O / CH2Cl2 / 1 h / 20 °C
3.1: 79 percent / Cs2CO3; Bu4NI / dimethylformamide / 2.5 h / 20 °C
4.1: 84 percent / TBAF*3H2O / tetrahydrofuran / 2 h / 0 °C
5.1: 88 percent / PPh3; CBr4 / acetonitrile / 20 °C
6.1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
7.1: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
8.1: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
9.1: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
10.1: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
11.1: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
12.1: Cs2CO3; Bu4NI / dimethylformamide / 2 h
13.1: 8.7 mg / pyridine / 3 h / 20 °C
14.1: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
15.1: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
16.1: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
17.1: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
18.1: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
935263-71-1

4-allyl-5-(4-hydroxy-3-methyl-but-2-enyl)-2-(4-methoxy-benzyloxy)-5-methyl-cyclopent-2-enone

146436-22-8

(−)-terpestacin

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 88 percent / PPh3; CBr4 / acetonitrile / 20 °C
2: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
3: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
4: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
5: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
6: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
7: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
8: Cs2CO3; Bu4NI / dimethylformamide / 2 h
9: 8.7 mg / pyridine / 3 h / 20 °C
10: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
11: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
12: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
13: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
14: 74 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
View Scheme
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