(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

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-dienal
• CAS No.: 301652-21-1
• Molecular Formula: C₆₃H₉₇NO₆SSi₃
• Molecular Weight: 1080.79
• Mol file: 301652-21-1.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-dienal

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-dienal

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-dienal

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-dienal 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)-1-hydroxy-4,4,6,8-tetramethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one → (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)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Multistep reaction; 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, -78 to 0 deg C, 30 min;

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-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-dienal (301652-21-1) → 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 7 steps

1: 4.24 g / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 2 h / 25 °C

2: 2.30 g / TBAF / tetrahydrofuran / 10 h / 0 - 25 °C

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

4: 4.7 g / DMAP / tetrahydrofuran; toluene / 1 h / 75 °C

5: 78 percent / HF*py; pyridine / tetrahydrofuran / 24 h / 0 - 25 °C

6: 67 percent / tert-BuOOH; (+)-diethyl L-tartrate; Ti(OiPr)4 / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 2 h / -30 °C

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

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; pyridine hydrogenfluoride; triethylamine; 4 A molecular sieve; In tetrahydrofuran; decane; dichloromethane; water; toluene; tert-butyl alcohol; 1: Oxidation / 2: Silyl ether cleavage / 3: Acylation / 4: Cyclization / 5: Ether cleavage / 6: Epoxidation / 7: Tosylation;

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

Downstream 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-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

(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