(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-al

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-al
CAS No.:343263-00-3
Molecular Formula:C₅₂H₉₀O₇SSi₃
Molecular Weight:943.605
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-al

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-al

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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-al

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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-al

There total 24 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-al 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:

: 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

: 343263-00-3
(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-al

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; for 1h;
DOI:10.1021/ol015753k

Reference yield:

: 994-30-9
triethylsilyl chloride

: 343263-00-3
(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-al

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / pyridine / CH₂Cl₂ / 3 h

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

3: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

With pyridine; n-butyllithium; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; 3: Dess-Martin oxidation;
DOI:10.1021/ol015753k

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 343263-00-3
(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-al

Guidance literature:: Multi-step reaction with 8 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

8: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

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 / 8: Dess-Martin oxidation;
DOI:10.1021/ol015753k