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139220-18-1

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Basic Information
CAS No.: 139220-18-1
Name: 4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S)-
Article Data: 3
Molecular Structure:
Molecular Structure of 139220-18-1 (4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrien-1-yl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S)-)
Formula: C31H45 N3 O4 S
Molecular Weight: 555.782
Synonyms: 4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrienyl]-9,11,17-trimethyl-,(3S,6Z,8E,11S,15R,17S)- (9CI);4,12-Dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraene-5,13-dione,15-amino-3-[7-(dimethylamino)-2,5-dimethyl-1,3,5-heptatrienyl]-9,11,17-trimethyl-,[3S-[3R*(1E,3E,5E),6Z,8E,11R*,15S*,17R*]]-; (-)-Pateamine; (-)-Pateamine A;Pateamine; Pateamine A
PSA: 122.99000
LogP: 6.35700
Related products
Synthetic route
201339-93-7

C36H50Cl3N3O6S

139220-18-1

(-)-pateamine

Conditions
ConditionsYield
With 10% Cd/Pd; ammonium acetate In tetrahydrofuran at 25℃; for 3.5h;78%
With ammonium acetate; 10% Cd/Pd In tetrahydrofuran at 20℃; for 5h; Hydrolysis;73%
With ammonium acetate; Cd/Pd In tetrahydrofuran at 20℃; for 3h;73%
693790-26-0

[(6Z,8E)-(3S,11S,15R,17S)-3-(tert-butyldimethylsilanyloxymethyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl]carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 78 percent / TBAF / tetrahydrofuran / 20 h / 20 °C
2: 70 percent / Dess-Martin periodinane / CH2Cl2 / 3.5 h / 0 - 20 °C
3: 73 percent / benzene / 3 h / Heating
4: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
5: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
View Scheme
308240-84-8

((6Z,8E)-(3S,11S,15R,17S)-3-formyl-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 73 percent / benzene / 3 h / Heating
2: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
3: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 73 percent / 3 h / Heating
2: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
3: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
4: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
308240-96-2

((6Z,8E)-(3S,11S,15R,17S)-3-hydroxymethyl-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 70 percent / Dess-Martin periodinane / CH2Cl2 / 3.5 h / 0 - 20 °C
2: 73 percent / benzene / 3 h / Heating
3: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
4: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
2: 73 percent / 3 h / Heating
3: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
4: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
5: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
308240-85-9

((6Z,8E)-(3S,11S,15R,17S)-9,11,17-trimethyl-3-((E)-2-methyl-3-oxopropenyl)-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
2: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
2: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
3: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
308240-76-8

((6Z,8E)-(3S,11S,15R,17S)-3-((1E,3E)-4-iodo-2-methylbuta-1,3-dienyl)-9,11,17-trimethyl-5,13-dioxo-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]heneicosa-1(21),6,8,18-tetraen-15-yl)carbamic acid 2,2,2-trichloro-1,1-dimethyl ester

139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / aq. NH4OAc / Cd/Pd / tetrahydrofuran / 3 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
2: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
308240-90-6

(+)-(S)-4-tert-Butyldimethylsilyloxy-3-methyl-2-butanone

139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1.1: LiHMDS / -78 °C
1.2: 86 percent / TMSCl; Br2
2.1: 2,6-lutidene / CH2Cl2 / 12 h / 20 °C
3.1: (CF3CO)2O; pyridine / CH2Cl2 / 0.5 h / -30 °C
4.1: 92 percent / AcOH / tetrahydrofuran; H2O / 12 h / 20 °C
5.1: Et3N / CH2Cl2 / 1 h / 0 °C
6.1: dimethylsulfoxide / 6 h / 60 °C
7.1: 85 percent / DIBAL / toluene / 2 h / 0 °C
8.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
9.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
10.1: 95 percent / TFA / methanol / 4 h / 20 °C
11.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
12.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
13.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
13.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
14.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
15.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
16.1: 73 percent / 3 h / Heating
17.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
18.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
19.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
308240-79-1

(S)-1-bromo-4-(tert-butyldimethylsilanyloxy)-3-methylbutan-2-one

139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: 2,6-lutidene / CH2Cl2 / 12 h / 20 °C
2.1: (CF3CO)2O; pyridine / CH2Cl2 / 0.5 h / -30 °C
3.1: 92 percent / AcOH / tetrahydrofuran; H2O / 12 h / 20 °C
4.1: Et3N / CH2Cl2 / 1 h / 0 °C
5.1: dimethylsulfoxide / 6 h / 60 °C
6.1: 85 percent / DIBAL / toluene / 2 h / 0 °C
7.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
8.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
9.1: 95 percent / TFA / methanol / 4 h / 20 °C
10.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
11.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
12.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
12.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
13.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
14.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
15.1: 73 percent / 3 h / Heating
16.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
17.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
18.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
308240-93-9

(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyraldehyde

139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
2.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
3.1: 95 percent / TFA / methanol / 4 h / 20 °C
4.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
5.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
6.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
6.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
7.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
8.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
9.1: 73 percent / 3 h / Heating
10.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
11.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
12.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
308240-81-5

(S)-3-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-butyronitrile

139220-18-1

(-)-pateamine

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 85 percent / DIBAL / toluene / 2 h / 0 °C
2.1: 64 percent / Ti(OEt)4 / CH2Cl2 / 4 h / 50 °C
3.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C
4.1: 95 percent / TFA / methanol / 4 h / 20 °C
5.1: 89 percent / pyridine / CH2Cl2 / 2 h / 0 °C
6.1: 87 percent / DDQ / CH2Cl2; H2O / 2 h / 20 °C
7.1: 2,4,6-trichlorobenzoyl chloride; Et3N; DMAP / toluene / 1 h / -30 °C
7.2: Pd(dba)2; Ph3As / dimethylformamide / 1 h / 55 °C
8.1: 78 percent / TBAF / acetic acid; tetrahydrofuran / 24 h / 20 °C
9.1: 70 percent / Dess-Martin reagent; pyridine / CH2Cl2 / 2 h / 20 °C
10.1: 73 percent / 3 h / Heating
11.1: 68 percent / CrCl2 / tetrahydrofuran / 1.5 h / 20 °C
12.1: 36 percent / Pd(CH3CN)2Cl2 / dimethylformamide / 6 h / 20 °C
13.1: 73 percent / NH4OAc / Cd-Pb / tetrahydrofuran / 5 h / 20 °C
View Scheme
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    139220-18-1

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