Epothilone D supplier | CasNO.189453-10-9

Name
Epothilone D
EINECS
CAS No. 189453-10-9
Article Data36
CAS DataBase
Density 1.085 g/cm³
Solubility
Melting Point 63-66°C
Formula C₂₇H₄₁NO₅S
Boiling Point 663.658 °C at 760 mmHg
Molecular Weight 491.692
Flash Point 355.168 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Oxacyclohexadec-13-ene-2,6-dione,4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-,[4S-[4R*,7S*,8R*,9R*,13Z,16R*(E)]]-;(-)-Desoxyepothilone B;(-)-Epothilone D;12,13-Deoxyepothilone B;12,13-Desoxyepothilone B;Desoxyepothilone B;Epo D;KOS 862;NSC 703147;
PSA 124.96000
LogP 4.87620

Synthetic route

: 241129-41-9
12,13-deoxy-3-(triethylsilyloxy)epothilone B

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
With pyridine hydrogenfluoride In tetrahydrofuran	98%
With pyridine hydrogenfluoride In tetrahydrofuran at 0℃; for 5h;	91%

: 189453-35-8
(4S,7R,8S,9S,13Z,16S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
With pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 36h;	96%
With pyridine; pyridine hydrogenfluoride In tetrahydrofuran at 0 - 20℃; for 36h;	96%
With pyridine hydrogenfluoride In tetrahydrofuran	92%

: 219823-99-1
(13Z,4S,7R,8S,9S,16S)-4-(tert-butyldimethylsilyloxy)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]oxacyclohexadec-13-ene-2,6-dione

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
With pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 16h;	95%
With trifluoroacetic acid In dichloromethane at 0℃; for 1.5h;	69%

: 189453-51-8
(Z)-(4S,6R,7S,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4,6-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-en-2-one

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
With pyridine hydrogenfluoride In tetrahydrofuran at 0 - 20℃; for 2h; desilylation;	92%
Multi-step reaction with 3 steps 1: 89 percent / 2,6-lutidine / CH2Cl2 / -30 °C 2: 67 percent / Dess-Martin periodinane / CH2Cl2 / Ambient temperature 3: 80 percent / HF*pyridine / tetrahydrofuran / Ambient temperature View Scheme

: 380605-94-7
Carbonic acid (Z)-(4S,7R,8S,9S,16S)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
With ammonium chloride; zinc In methanol Heating;	92%

: 350493-61-7
(E)-9,10-dehydro-12,13-desoxyepothilone B

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
With TrisNHNH2; triethylamine In 1,2-dichloro-ethane at 50℃; for 7h;	91%
With TrisNHNH2; triethylamine In 1,2-dichloro-ethane at 50℃; for 7h;	91%
With potassium diazodicarboxylate; acetic acid In 1,2-dichloro-ethane at 45℃;	60%

: 371979-40-7
10,11-didehydroepothilone D

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
With potassium diazodicarboxylate; acetic acid In dichloromethane Heating;	86%

: 152044-54-7
epothilone B

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
With n-butyllithium; tungsten(VI) chloride In tetrahydrofuran deoxygenation;	78%

: 220889-57-6
7-[(1E)-1-methyl-2-(2-methyl(1,3-thiazol-4-yl))vinyl]-(3S,7S,14S,15S,16R)-3,15-dihydroxy-2,2,10,14,16-pentamethyl-6-oxacyclohexadeca-9,12-diene-1,5-dione

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
With trisylhydrazine; triethylamine In diethyl ether at 39℃;	71%
With trisylhydrazine; triethylamine In 1,2-dichloro-ethane at 50℃; for 18h;	70%
With potassium diazodicarboxylate; acetic acid In dichloromethane for 24h; Heating;	52%
With potassium diazodicarboxylate; acetic acid In dichloromethane for 25h; Heating;	52%

: 204195-20-0
(Z)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

A: 189453-10-9
epothilone D

B: 189453-40-5
E-epothilone D

Conditions

Conditions	Yield
With pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 1.5h; desilylation;
With trifluoroacetic acid In dichloromethane at 0 - 20℃;
With pyridine; hydrogen fluoride In tetrahydrofuran at 20℃;

: 823789-81-7
(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: pyridine / CH2Cl2 / 1 h / 0 °C 2.1: CH2Cl2 / 5 h / 20 °C 3.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 4.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 5.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 6.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 7.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: pyridine / CH2Cl2 / 1 h / 0 °C
2.1: CH2Cl2 / 5 h / 20 °C
3.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
4.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
5.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
6.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
7.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

: 380605-92-5
(12Z,16E)-(3S,6R,7S,8S,15S)-3-(tert-Butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 1.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 2.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 3.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

: C45H85NO7SSi3

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: CH2Cl2 / 5 h / 20 °C 2.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 3.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 4.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 5.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 6.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: CH2Cl2 / 5 h / 20 °C
2.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
3.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
4.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
5.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
6.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

: 823789-87-3
(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-[(2,2,2-trichloroethoxycarbonyl)oxy]-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 2.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 3.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 4.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
2.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
3.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
4.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

: C48H86Cl3NO9SSi3

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 2.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 3.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 4.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 5.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
2.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
3.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
4.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
5.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

: 76632-23-0
4-(hydroxymethyl)-2-methylthiazole

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C 2.1: 86 percent / 3 h / 160 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 4.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 4.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 5.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 6.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 6.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 7.1: pyridine / CH2Cl2 / 1 h / 0 °C 8.1: CH2Cl2 / 5 h / 20 °C 9.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 10.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 11.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 11.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 12.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 13.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

Yield

Multi-step reaction with 13 steps
1.1: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C
2.1: 86 percent / 3 h / 160 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
3.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
4.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
4.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
5.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
6.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
6.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
7.1: pyridine / CH2Cl2 / 1 h / 0 °C
8.1: CH2Cl2 / 5 h / 20 °C
9.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
10.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
11.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
11.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
12.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
13.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

: 39238-07-8
4-(chloromethyl)-2-methyl-1,3-thiazole

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 86 percent / 6 h / 160 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 3.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 3.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 4.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 5.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 6.1: pyridine / CH2Cl2 / 1 h / 0 °C 7.1: CH2Cl2 / 5 h / 20 °C 8.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 9.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 10.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 11.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 12.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 11 steps 1.1: 84 percent / 2 h / 165 °C 2.1: tBuOK / tetrahydrofuran 2.2: 75 percent / tetrahydrofuran / 4 h / -30 - 20 °C 3.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C 4.1: NaBH4 / methanol 5.1: CBr4; PPh3 / acetonitrile / 0 °C 5.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C 6.1: tetrahydrofuran / -78 °C 7.1: LiHMDS / tetrahydrofuran / -78 °C 7.2: 80 percent / tetrahydrofuran 8.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 8.2: 85 percent / nBu4NF / tetrahydrofuran 9.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 9.2: 60 percent / DMAP / toluene / 80 °C 10.1: 86 percent / TFA / CH2Cl2 / 0 °C 11.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme
Multi-step reaction with 18 steps 1.1: 97 percent / benzene / 8 h / Heating 2.1: 10.95 g / LiHMDS / tetrahydrofuran / 0.67 h / 55 °C 3.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - 20 °C 4.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h 4.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C 5.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C 6.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C 7.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C 7.2: 93 percent / tetrahydrofuran / 1 h / -78 °C 8.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C 9.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C 10.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C 11.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C 11.2: tetrahydrofuran / 1.5 h / -95 - -80 °C 12.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 13.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C 14.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C 15.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 16.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 17.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide HCl; DMAP; DMAPHCl / CHCl3 / 17 h / Heating 18.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: 4 h / Reflux 2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C 2.2: 2 h / -78 - -20 °C 3.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C View Scheme

: 6436-59-5
ethyl 2-methylthiazole-4-carboxylate

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1.1: 84 percent / LiAlH4 / diethyl ether / 3 h / -78 °C 2.1: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C 3.1: 86 percent / 3 h / 160 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 5.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 5.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 6.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 7.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 8.1: pyridine / CH2Cl2 / 1 h / 0 °C 9.1: CH2Cl2 / 5 h / 20 °C 10.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 11.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 12.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 13.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 14.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 23 steps 1: 90 percent / DIBAL / CH2Cl2 / 1 h / -78 °C 2: 98 percent / benzene / 2 h / Heating 3: 74 percent / diethyl ether; pentane / 1 h / -100 °C 4: 99 percent / imidazole / dimethylformamide / 1) 0 deg C, 45 min, 2) 25 deg C, 2.5 h 5: 95 percent / 4-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 1) 0 deg C, 2.5 h, 2) 25 deg C, 12 h 6: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 7: 95 percent / benzene / 3 h / Heating 8: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 9: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 10: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 11: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 12: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 13: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 14: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 15: 82 percent / DIBAL / toluene / 1 h / -78 °C 16: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 17: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 18: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C 19: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min 20: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature 21: 73 percent / TBAF / tetrahydrofuran / 8 h / 25 °C 22: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 25 deg C, 15 min, 2) toluene, 25 deg C, 12 h 23: 91 percent / CF3CO2H / CH2Cl2 / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h View Scheme

Yield

Multi-step reaction with 14 steps
1.1: 84 percent / LiAlH4 / diethyl ether / 3 h / -78 °C
2.1: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C
3.1: 86 percent / 3 h / 160 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
5.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
5.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
6.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
7.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
8.1: pyridine / CH2Cl2 / 1 h / 0 °C
9.1: CH2Cl2 / 5 h / 20 °C
10.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
11.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
12.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
13.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
14.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

Multi-step reaction with 23 steps
1: 90 percent / DIBAL / CH2Cl2 / 1 h / -78 °C
2: 98 percent / benzene / 2 h / Heating
3: 74 percent / diethyl ether; pentane / 1 h / -100 °C
4: 99 percent / imidazole / dimethylformamide / 1) 0 deg C, 45 min, 2) 25 deg C, 2.5 h
5: 95 percent / 4-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 1) 0 deg C, 2.5 h, 2) 25 deg C, 12 h
6: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C
7: 95 percent / benzene / 3 h / Heating
8: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C
9: 83 percent / Ph3P, CCl4 / 24 h / 100 °C
10: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C
11: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C
12: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C
13: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h
14: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C
15: 82 percent / DIBAL / toluene / 1 h / -78 °C
16: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min
17: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
18: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C
19: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min
20: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature
21: 73 percent / TBAF / tetrahydrofuran / 8 h / 25 °C
22: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 25 deg C, 15 min, 2) toluene, 25 deg C, 12 h
23: 91 percent / CF3CO2H / CH2Cl2 / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h
View Scheme

: 63928-37-0
diethyl (2-methyl-1,3-thiazol-4-yl)methylphosphonate

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 2.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 2.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 3.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 4.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 5.1: pyridine / CH2Cl2 / 1 h / 0 °C 6.1: CH2Cl2 / 5 h / 20 °C 7.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 8.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 9.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 10.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 11.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 10 steps 1.1: tBuOK / tetrahydrofuran 1.2: 75 percent / tetrahydrofuran / 4 h / -30 - 20 °C 2.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C 3.1: NaBH4 / methanol 4.1: CBr4; PPh3 / acetonitrile / 0 °C 4.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C 5.1: tetrahydrofuran / -78 °C 6.1: LiHMDS / tetrahydrofuran / -78 °C 6.2: 80 percent / tetrahydrofuran 7.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 7.2: 85 percent / nBu4NF / tetrahydrofuran 8.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 8.2: 60 percent / DMAP / toluene / 80 °C 9.1: 86 percent / TFA / CH2Cl2 / 0 °C 10.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme
Multi-step reaction with 11 steps 1: 74 percent / n-BuLi 2: DIBAL-H 3: Dess-Martin periodinane 4: 67 percent / Li(i-Pr)2N / -78 °C 5: 79 percent / Cl2CHCO2H 6: Dess-Martin periodinane 7: NaClO2 8: MgBr2; n-BuSH; K2CO3 9: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 10: 91 percent / CF3CO2H / CH2Cl2 View Scheme

: 106921-60-2
2,2-dimethyl-3-oxopentanal

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 88 percent / Bu2BOTf; DIPEA / CH2Cl2 / 1 h / -78 °C 2.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3.1: 76 percent / lithium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 4 h / 20 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 4.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 5.1: pyridine / CH2Cl2 / 1 h / 0 °C 6.1: CH2Cl2 / 5 h / 20 °C 7.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 8.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 9.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 10.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 11.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 14 steps 1.1: 68 percent / (-)-Ipc2BOMe / diethyl ether / -100 °C 2.1: i-Pr2NH; n-BuLi / tetrahydrofuran; hexane / 0.83 h / -78 °C 2.2: 61 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.1: 89 percent / Et3N / CH2Cl2 / 0.75 h / 0 °C 4.1: OsO4; NaIO4 / tetrahydrofuran; H2O / 18 h 5.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1 h 6.1: 502 mg / methanol; benzene; hexane / 0.75 h 7.1: 92 percent / H2 / Pd/C / ethanol / 0.75 h 8.1: 99 percent / TPAP; NMO / CH2Cl2 / 1 h 9.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C 9.2: 82 percent / tetrahydrofuran; hexane / 70 h / -78 - 20 °C 10.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 11.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 12.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 12.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 13.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 14.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating View Scheme
Multi-step reaction with 16 steps 1.1: 68 percent / (-)-Ipc2BOMe / diethyl ether / -100 °C 2.1: i-Pr2NH; n-BuLi / tetrahydrofuran; hexane / 0.83 h / -78 °C 2.2: 61 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.1: 89 percent / Et3N / CH2Cl2 / 0.75 h / 0 °C 4.1: OsO4; NaIO4 / tetrahydrofuran; H2O / 18 h 5.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1 h 6.1: 502 mg / methanol; benzene; hexane / 0.75 h 7.1: 92 percent / H2 / Pd/C / ethanol / 0.75 h 8.1: 99 percent / TPAP; NMO / CH2Cl2 / 1 h 9.1: t-BuOK / tetrahydrofuran / 5 h / -78 °C 9.2: 80 percent / tetrahydrofuran / 12 h / -78 °C 10.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C 10.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C 11.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 12.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 13.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 14.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 14.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 15.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 16.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating View Scheme
Multi-step reaction with 6 steps 1.1: Bu2BOTf; DIPEA / CH2Cl2 / -78 - 0 °C 1.2: 70 percent / Raney Ni / acetone / 0.75 h / 60 °C 2.1: 2,6-lutidine / CH2Cl2 / 0 - 20 °C 2.2: LiOH; H2O2 / tetrahydrofuran; H2O / 20 °C 3.1: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 4.1: 95 percent / HF / pyridine; CH2Cl2 / 20 °C 5.1: 92 percent / Zn; aq. NH4Cl / methanol / Heating View Scheme
Multi-step reaction with 13 steps 1: 74 percent / diethyl ether / 0.5 h / -100 °C 2: 98 percent / 2,6-lutidine / CH2Cl2 / 0.75 h / -78 °C 3: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 4: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 5: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 6: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 7: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 8: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C 9: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min 10: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature 11: 73 percent / TBAF / tetrahydrofuran / 8 h / 25 °C 12: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 25 deg C, 15 min, 2) toluene, 25 deg C, 12 h 13: 91 percent / CF3CO2H / CH2Cl2 / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h View Scheme

: 187283-45-0
(S)-3-((tert-butyldimethylsilyl)oxy)-4,4-dimethyl-5-oxoheptanoic acid

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 1.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 2.1: pyridine / CH2Cl2 / 1 h / 0 °C 3.1: CH2Cl2 / 5 h / 20 °C 4.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 5.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 6.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 7.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 8.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 2: 95 percent / HF / pyridine; CH2Cl2 / 20 °C 3: 92 percent / Zn; aq. NH4Cl / methanol / Heating View Scheme
Multi-step reaction with 5 steps 1.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 1.3: 3 h / -78 - 20 °C / Inert atmosphere 2.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere 4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere 2.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere 2.2: 15 h / -12 °C / Inert atmosphere 3.1: 2,6-dimethylpyridine / dichloromethane / 5 h / -45 - 20 °C / Inert atmosphere 4.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 2 h / -20 - 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 6 steps 1: phenyltrimethylammonium tribromide / tetrahydrofuran / 1.25 h / 0 - 20 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 3: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 2.5 h / 0 °C 4: triethylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 1 h / 0 °C / Inert atmosphere 5: lithium iodide; chromium dichloride / tetrahydrofuran / 3.33 h / 20 °C / Inert atmosphere 6: trifluoroacetic acid / dichloromethane / 1.5 h / 0 °C View Scheme

: 380605-86-7
(-)-(2R,3S,5Z)-2-(4-methoxybenzyloxy)-6,10-dimethylundeca-5,10-dien-3-ol

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1.1: 92 percent / DIPEA / CH2Cl2 / 6 h / 20 °C 2.1: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 3 h / 20 °C 3.1: 85 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 5.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 5.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 6.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 7.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 8.1: pyridine / CH2Cl2 / 1 h / 0 °C 9.1: CH2Cl2 / 5 h / 20 °C 10.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 11.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 12.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 13.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 14.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 10 steps 1: 92 percent / DIPEA; DCM / 0 °C 2: 88 percent / DDQ / H2O 3: 85 percent / DMSO; (COCl)2; DCM / triethylamine / -78 °C 4: 72 percent / n-BuLi / tetrahydrofuran 5: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h 6: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C 7: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 8: 95 percent / HF / pyridine; CH2Cl2 / 20 °C 9: 92 percent / Zn; aq. NH4Cl / methanol / Heating View Scheme

Yield

Multi-step reaction with 14 steps
1.1: 92 percent / DIPEA / CH2Cl2 / 6 h / 20 °C
2.1: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 3 h / 20 °C
3.1: 85 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
5.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
5.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
6.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
7.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
8.1: pyridine / CH2Cl2 / 1 h / 0 °C
9.1: CH2Cl2 / 5 h / 20 °C
10.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
11.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
12.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
13.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
14.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

Multi-step reaction with 10 steps
1: 92 percent / DIPEA; DCM / 0 °C
2: 88 percent / DDQ / H2O
3: 85 percent / DMSO; (COCl)2; DCM / triethylamine / -78 °C
4: 72 percent / n-BuLi / tetrahydrofuran
5: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h
6: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
7: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
8: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
9: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme

: 380605-89-0
(Z)-(S)-6,10-Dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-5,10-dien-2-one

: 189453-10-9
epothilone D

Conditions

Yield

Multi-step reaction with 11 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
2.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
2.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
3.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
4.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
5.1: pyridine / CH2Cl2 / 1 h / 0 °C
6.1: CH2Cl2 / 5 h / 20 °C
7.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
8.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
9.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
10.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
11.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

Multi-step reaction with 7 steps
1: 72 percent / n-BuLi / tetrahydrofuran
2: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h
3: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
4: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
5: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
6: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme

: 380605-88-9
(Z)-(2R,3S)-6,10-Dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-5,10-dien-2-ol

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 85 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 3.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 3.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 4.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 5.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 6.1: pyridine / CH2Cl2 / 1 h / 0 °C 7.1: CH2Cl2 / 5 h / 20 °C 8.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 9.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 10.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 11.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 12.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1: 85 percent / DMSO; (COCl)2; DCM / triethylamine / -78 °C 2: 72 percent / n-BuLi / tetrahydrofuran 3: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h 4: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C 5: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 6: 95 percent / HF / pyridine; CH2Cl2 / 20 °C 7: 92 percent / Zn; aq. NH4Cl / methanol / Heating View Scheme

Yield

Multi-step reaction with 12 steps
1.1: 85 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
3.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
3.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
4.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
5.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
6.1: pyridine / CH2Cl2 / 1 h / 0 °C
7.1: CH2Cl2 / 5 h / 20 °C
8.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
9.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
10.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
11.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
12.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

Multi-step reaction with 8 steps
1: 85 percent / DMSO; (COCl)2; DCM / triethylamine / -78 °C
2: 72 percent / n-BuLi / tetrahydrofuran
3: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h
4: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
5: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
6: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
7: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme

: 380605-87-8
(2-{1-[1-(4-methoxy-benzyloxy)-ethyl]-4,8-dimethyl-nona-3,8-dienyloxymethoxy}-ethyl)-trimethyl-silane

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 3 h / 20 °C 2.1: 85 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 4.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 4.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 5.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 6.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 6.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 7.1: pyridine / CH2Cl2 / 1 h / 0 °C 8.1: CH2Cl2 / 5 h / 20 °C 9.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 10.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 11.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 11.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 12.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 13.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1: 88 percent / DDQ / H2O 2: 85 percent / DMSO; (COCl)2; DCM / triethylamine / -78 °C 3: 72 percent / n-BuLi / tetrahydrofuran 4: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h 5: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C 6: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 7: 95 percent / HF / pyridine; CH2Cl2 / 20 °C 8: 92 percent / Zn; aq. NH4Cl / methanol / Heating View Scheme

Yield

Multi-step reaction with 13 steps
1.1: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 3 h / 20 °C
2.1: 85 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
3.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
4.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
4.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
5.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
6.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
6.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
7.1: pyridine / CH2Cl2 / 1 h / 0 °C
8.1: CH2Cl2 / 5 h / 20 °C
9.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
10.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
11.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
11.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
12.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
13.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

Multi-step reaction with 9 steps
1: 88 percent / DDQ / H2O
2: 85 percent / DMSO; (COCl)2; DCM / triethylamine / -78 °C
3: 72 percent / n-BuLi / tetrahydrofuran
4: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h
5: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
6: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
7: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
8: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme

: 380605-90-3
2-methyl-4-[2,6,10-trimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-1,5,10-trienyl]-thiazole

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 1.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 2.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 3.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 4.1: pyridine / CH2Cl2 / 1 h / 0 °C 5.1: CH2Cl2 / 5 h / 20 °C 6.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 7.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 8.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 8.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 9.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 10.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h 2: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C 3: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 4: 95 percent / HF / pyridine; CH2Cl2 / 20 °C 5: 92 percent / Zn; aq. NH4Cl / methanol / Heating View Scheme

Yield

Multi-step reaction with 10 steps
1.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
1.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
2.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
3.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
4.1: pyridine / CH2Cl2 / 1 h / 0 °C
5.1: CH2Cl2 / 5 h / 20 °C
6.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
7.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
8.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
8.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
9.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
10.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

Multi-step reaction with 6 steps
1: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h
2: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
3: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
4: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
5: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme

: 380605-93-6
Carbonic acid (Z)-(4S,7R,8S,9S,16S)-4-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 2: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 95 percent / HF / pyridine; CH2Cl2 / 20 °C 2: 92 percent / Zn; aq. NH4Cl / methanol / Heating View Scheme

: 380605-84-5
(+)-(2S,6Z,9S,10E)-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxymethoxy)undeca-6,10-dienal

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 1.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 2.1: pyridine / CH2Cl2 / 1 h / 0 °C 3.1: CH2Cl2 / 5 h / 20 °C 4.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 5.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 6.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 7.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 8.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1: 67 percent / Li(i-Pr)2N / -78 °C 2: 79 percent / Cl2CHCO2H 3: Dess-Martin periodinane 4: NaClO2 5: MgBr2; n-BuSH; K2CO3 6: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 7: 91 percent / CF3CO2H / CH2Cl2 View Scheme
Multi-step reaction with 4 steps 1: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 2: 95 percent / HF / pyridine; CH2Cl2 / 20 °C 3: 92 percent / Zn; aq. NH4Cl / methanol / Heating View Scheme
Multi-step reaction with 8 steps 1.1: lithium diisopropyl amide; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 40 °C 1.2: 0.03 h / -78 °C 2.1: 2,6-dimethylpyridine / dichloromethane / 6 h / 0 °C 3.1: dichloro-acetic acid / dichloromethane / 2 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 5.1: sodium chlorite; sodium dihydrogenphosphate; 2,3-Dimethyl-2-butene / tetrahydrofuran; water; tert-butyl alcohol / 1 h / 20 °C 6.1: potassium carbonate; magnesium bromide ethyl etherate; n-butanethiol / diethyl ether / 2 h / 20 °C 7.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.75 h / 0 °C 7.2: 5 h / 75 °C 8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C View Scheme

: 380605-91-4
(2S,9S,6Z,10E)-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxy)methoxyundeca-6,10-dien-1-ol

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 2.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 3.1: pyridine / CH2Cl2 / 1 h / 0 °C 4.1: CH2Cl2 / 5 h / 20 °C 5.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 6.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 7.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 8.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 9.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1: Dess-Martin periodinane 2: 67 percent / Li(i-Pr)2N / -78 °C 3: 79 percent / Cl2CHCO2H 4: Dess-Martin periodinane 5: NaClO2 6: MgBr2; n-BuSH; K2CO3 7: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 8: 91 percent / CF3CO2H / CH2Cl2 View Scheme
Multi-step reaction with 5 steps 1: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C 2: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 3: 95 percent / HF / pyridine; CH2Cl2 / 20 °C 4: 92 percent / Zn; aq. NH4Cl / methanol / Heating View Scheme
Multi-step reaction with 9 steps 1.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 2.1: lithium diisopropyl amide; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 40 °C 2.2: 0.03 h / -78 °C 3.1: 2,6-dimethylpyridine / dichloromethane / 6 h / 0 °C 4.1: dichloro-acetic acid / dichloromethane / 2 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C 6.1: sodium chlorite; sodium dihydrogenphosphate; 2,3-Dimethyl-2-butene / tetrahydrofuran; water; tert-butyl alcohol / 1 h / 20 °C 7.1: potassium carbonate; magnesium bromide ethyl etherate; n-butanethiol / diethyl ether / 2 h / 20 °C 8.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.75 h / 0 °C 8.2: 5 h / 75 °C 9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C View Scheme

: 250679-52-8
(3S)-3-[((tert-butyl)dimethylsilyl)oxy]-1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.01.5]dec-4-yl]-4,4-dimethylheptan-1,5-dione

: 189453-10-9
epothilone D

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: 76 percent / lithium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 4 h / 20 °C 2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 2.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 3.1: pyridine / CH2Cl2 / 1 h / 0 °C 4.1: CH2Cl2 / 5 h / 20 °C 5.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 6.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 7.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 8.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 9.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 24.5 h / 0 - 25 °C / Inert atmosphere 2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere 3.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere 3.2: 15 h / -12 °C / Inert atmosphere 4.1: 2,6-dimethylpyridine / dichloromethane / 5 h / -45 - 20 °C / Inert atmosphere 5.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere 6.1: trifluoroacetic acid / dichloromethane / 2 h / -20 - 0 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 9 steps
1.1: 76 percent / lithium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 4 h / 20 °C
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
2.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
3.1: pyridine / CH2Cl2 / 1 h / 0 °C
4.1: CH2Cl2 / 5 h / 20 °C
5.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
6.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
7.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
8.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
9.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme

Multi-step reaction with 6 steps
1.1: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 24.5 h / 0 - 25 °C / Inert atmosphere
2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere
3.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere
3.2: 15 h / -12 °C / Inert atmosphere
4.1: 2,6-dimethylpyridine / dichloromethane / 5 h / -45 - 20 °C / Inert atmosphere
5.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
6.1: trifluoroacetic acid / dichloromethane / 2 h / -20 - 0 °C / Inert atmosphere
View Scheme

: 189453-10-9
epothilone D

: 152044-54-7
epothilone B

Conditions

Conditions	Yield
With 3,3-dimethyldioxirane In dichloromethane at -50℃;	98%
With 3,3-dimethyldioxirane In dichloromethane; acetone at -78 - -50℃; for 2.5h; Epoxidation;	97%
With 3,3-dimethyldioxirane In dichloromethane at -35℃;	97%

: 69739-34-0
t-butyldimethylsiyl triflate

: 189453-10-9
epothilone D

: 189453-35-8
(4S,7R,8S,9S,13Z,16S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -78℃;	85%
With 2,6-dimethylpyridine In dichloromethane at 0℃; silylation;

: 189453-10-9
epothilone D

: C27H42N2O5S

Conditions

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; O-(2,4-dinitrophenyl)hydroxylamine at 25℃; for 4h; Inert atmosphere;	70%

: 189453-10-9
epothilone D

A: 152044-54-7
epothilone B

B: (1R,3S,7S,10R,11S,12S,16S)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

Conditions

Conditions	Yield
With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate In water; acetonitrile at 0℃;	A 69% B n/a
With 3,3-dimethyldioxirane In dichloromethane; acetone at -78 - -50℃;	A 53% B n/a
With 3-chloro-benzenecarboperoxoic acid In chloroform at -10 - 0℃; for 5h;	A 30% B n/a

: 189453-10-9
epothilone D

: (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4-oxa-17-azabicyclo[14.1.0]heptadecane-5,9-dione

Conditions

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; O-(2,4-dinitrophenyl)hydroxylamine In 2,2,2-trifluoroethanol at 25℃; for 4h; Inert atmosphere;	66%
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; O-(2,4-dinitrophenyl)hydroxylamine In 2,2,2-trifluoroethanol at 25℃; for 4h;	66%

Epothilone D Specification

The Epothilone D, with the CAS registry number 189453-10-9, is also known as 12,13-Deoxyepothilone B. It belongs to the product categories of Inhibitors; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds. This chemical's molecular formula is C₂₇H₄₁NO₅S and molecular weight is 491.68. What's more, its systematic name is (4S,7R,8S,9S,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]oxacyclohexadec-13-ene-2,6-dione.

Physical properties of Epothilone D are: (1)ACD/LogP: 1.724; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.72; (4)ACD/LogD (pH 7.4): 1.72; (5)ACD/BCF (pH 5.5): 12.02; (6)ACD/BCF (pH 7.4): 12.04; (7)ACD/KOC (pH 5.5): 206.33; (8)ACD/KOC (pH 7.4): 206.56; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 124.96 Å²; (13)Index of Refraction: 1.522; (14)Molar Refractivity: 138.415 cm³; (15)Molar Volume: 453.292 cm³; (16)Polarizability: 54.872×10^-24cm³; (17)Surface Tension: 39.03 dyne/cm; (18)Density: 1.085 g/cm³; (19)Flash Point: 355.168 °C; (20)Enthalpy of Vaporization: 102.554 kJ/mol; (21)Boiling Point: 663.658 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1[C@H](C)[C@@H](O)[C@@H](C)CCCC(=C/C[C@H](OC(=O)C[C@H](O)C1(C)C)/C(=C/c2nc(sc2)C)C)\C
(2)Std. InChI: InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1
(3)Std. InChIKey: XOZIUKBZLSUILX-GIQCAXHBSA-N

Product Name

Epothilone D

Synthetic route

Epothilone D Specification

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