(-)-(3S,4E)-3-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-4-METHYL-5-(2-METHYL-1,3-THIAZOL-4-YL)PENT-4-EN-1-OL

Base Information

• Chemical Name: (-)-(3S,4E)-3-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-4-METHYL-5-(2-METHYL-1,3-THIAZOL-4-YL)PENT-4-EN-1-OL
• CAS No.: 188899-14-1
• Molecular Formula: C16H29NO2SSi
• Molecular Weight: 327.563
• Mol file: 188899-14-1.mol

Synonyms:(-)-(3S,4E)-3-{[tert-Butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol;

Chemical Property of (-)-(3S,4E)-3-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-4-METHYL-5-(2-METHYL-1,3-THIAZOL-4-YL)PENT-4-EN-1-OL

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• PSA: 70.59000
• LogP: 4.62760
• Solubility.: Dichloromethane, Ether, Ethyl Acetate, Hexane

Purity/Quality:

97% ^*data from raw suppliers

(-)-(3S,4E)-3-{[tert-Butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(3S,4E)-3-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-4-METHYL-5-(2-METHYL-1,3-THIAZOL-4-YL)PENT-4-EN-1-OL

There total 1 articles about (-)-(3S,4E)-3-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-4-METHYL-5-(2-METHYL-1,3-THIAZOL-4-YL)PENT-4-EN-1-OL 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:

ethyl 2-methylthiazole-4-carboxylate (6436-59-5) → (3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol (188899-14-1)

Guidance literature:

Multi-step reaction with 7 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: 96 percent / NaBH₄ / methanol / 0.25 h / 0 °C

With 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; osmium(VIII) oxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; benzene;

DOI:10.1021/ja971110h

Reference yield:

(3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol (188899-14-1) → epothilone B (152044-54-7)

Guidance literature:

Multi-step reaction with 17 steps

1.1: oxalyl chloride; DMSO; DIPEA / CH₂Cl₂ / -78 - 20 °C

2.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h

2.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C

3.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C

4.1: Ph₃P; imidazole; I₂ / acetonitrile; diethyl ether / 1 h / 20 °C

5.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C

5.2: 93 percent / tetrahydrofuran / 1 h / -78 °C

6.1: 65 percent / Na₂HPO₄; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C

7.1: 99 percent / CSA / methanol; CH₂Cl₂ / 5 h / 0 - 10 °C

8.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 4 h / 20 °C

9.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C

9.2: tetrahydrofuran / 1.5 h / -95 - -80 °C

10.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

11.1: 87 percent / CSA / methanol; CH₂Cl₂ / 4 h / 0 °C

12.1: Dess-Martin periodinane; Py / CH₂Cl₂ / 2 h / 20 °C

13.1: 380 mg / NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s); H₂O / 3 h

14.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

15.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl₃ / 17 h / Heating

16.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C

17.1: m-CPBA / CHCl₃ / 5 h / -18 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium amalgam; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; 4-(dimethylamino)pyridine hydrochloride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; n-heptane; dichloromethane; chloroform; water; acetonitrile; tert-butyl alcohol; 1.1: Swern oxidation / 2.2: Wittig olefination;

DOI:10.1021/jo0007480

Reference yield:

(3S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol (188899-14-1) → epothilone D (189453-10-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: oxalyl chloride; DMSO; DIPEA / CH₂Cl₂ / -78 - 20 °C

2.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h

2.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C

3.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C

4.1: Ph₃P; imidazole; I₂ / acetonitrile; diethyl ether / 1 h / 20 °C

5.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C

5.2: 93 percent / tetrahydrofuran / 1 h / -78 °C

6.1: 65 percent / Na₂HPO₄; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C

7.1: 99 percent / CSA / methanol; CH₂Cl₂ / 5 h / 0 - 10 °C

8.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 4 h / 20 °C

9.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C

9.2: tetrahydrofuran / 1.5 h / -95 - -80 °C

10.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

11.1: 87 percent / CSA / methanol; CH₂Cl₂ / 4 h / 0 °C

12.1: Dess-Martin periodinane; Py / CH₂Cl₂ / 2 h / 20 °C

13.1: 380 mg / NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s); H₂O / 3 h

14.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C

15.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl₃ / 17 h / Heating

16.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium amalgam; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; iodine; 4-(dimethylamino)pyridine hydrochloride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; n-heptane; dichloromethane; chloroform; water; acetonitrile; tert-butyl alcohol; 1.1: Swern oxidation / 2.2: Wittig olefination;

DOI:10.1021/jo0007480

upstream raw materials:

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

ethyl (2Z,5S,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate

epithilone A

desoxyepothilone A

Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-oxo-tridec-3-enyl ester

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