(5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-ol

Base Information

Chemical Name:(5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-ol
CAS No.:343262-80-6
Molecular Formula:C₅₂H₉₂O₇SSi₃
Molecular Weight:945.621
Hs Code.:

(5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-ol

Synonyms:(5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-ol

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Chemical Property of (5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-ol

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Technology Process of (5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-ol

There total 23 articles about (5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-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: 78.0%

: 75-21-8,99932-75-9
oxirane

: 343262-79-3
(2R,3S,4S,6R)-6-[(1S,7S,12S)-(2E,4E,8Z,10E)-14-benzenesulfonyl-1-(tert-butyldimethylsilanoxy)-12-triethylsilanoxy-5,7,9-trimethyltetradeca-2,4,8,10-tetraenyl]-4-(tert-butyldimethylsilanoxy)-3-methyl-2-E-propenyltetrahydropyran

: 343262-80-6
(5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃;
DOI:10.1021/ol015753k

Reference yield:

: 994-30-9
triethylsilyl chloride

: 343262-80-6
(5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / pyridine / CH₂Cl₂ / 3 h

2: 78 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With pyridine; n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1021/ol015753k

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 343262-80-6
(5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / imidazole; DMAP / dimethylformamide / 16 h

2: 99 percent / DIBAL / CH₂Cl₂ / 0.17 h / -78 °C

3: 93 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

4: 266 mg / t-BuOK; tributylphosphine / toluene; tetrahydrofuran / 0 °C

5: 89 percent / DIBAL / CH₂Cl₂ / 0.17 h / -78 °C

6: 94 percent / pyridine / CH₂Cl₂ / 3 h

7: 78 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With pyridine; 1H-imidazole; dmap; n-butyllithium; tributylphosphine; potassium tert-butylate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Dess-Martin oxidation;
DOI:10.1021/ol015753k