(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

Base Information

• Chemical Name: (12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid
• CAS No.: 301652-22-2
• Molecular Formula: C₆₃H₉₇NO₇SSi₃
• Molecular Weight: 1096.79
• Mol file: 301652-22-2.mol

Synonyms:(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

Chemical Property of (12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

There total 1 articles about (12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid 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:

(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienal (301652-21-1) → (12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid (301652-22-2)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; water; In tert-butyl alcohol; at 25 ℃; for 2h;

DOI:10.1039/a809954e

Reference yield:

(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid (301652-22-2) → (12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid (252986-91-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 12h; Yield given;

DOI:10.1039/a809954e

Reference yield:

(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid (301652-22-2) → Toluene-4-sulfonic acid (1S,3S,7S,10R,11S,12S,16S)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-2-(2-methyl-thiazol-4-yl)-vinyl]-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadec-16-ylmethyl ester

Guidance literature:

Multi-step reaction with 6 steps

1: 2.30 g / TBAF / tetrahydrofuran / 10 h / 0 - 25 °C

2: Et₃N / tetrahydrofuran / 1 h / 0 °C

3: 4.7 g / DMAP / tetrahydrofuran; toluene / 1 h / 75 °C

4: 78 percent / HF*py; pyridine / tetrahydrofuran / 24 h / 0 - 25 °C

5: 67 percent / tert-BuOOH; (+)-diethyl L-tartrate; Ti(OiPr)4 / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 2 h / -30 °C

6: Et₃N; DMAP / CH₂Cl₂ / 1 h / 0 - 25 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; pyridine hydrogenfluoride; triethylamine; 4 A molecular sieve; In tetrahydrofuran; decane; dichloromethane; toluene; 1: Silyl ether cleavage / 2: Acylation / 3: Cyclization / 4: Ether cleavage / 5: Epoxidation / 6: Tosylation;

DOI:10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B

upstream raw materials:

(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienal

Downstream raw materials:

(12E,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

(E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9-tetramethyl-16-[(E)-2-(2-methyl-thiazol-4-yl)-vinyl]-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione