(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-17-iodo-4,4,6,8,16-pentamethyl-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)-17-iodo-4,4,6,8,16-pentamethyl-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid
CAS No.:240816-01-7
Molecular Formula:C₆₀H₉₅IO₇Si₃
Molecular Weight:1139.57
Hs Code.:

(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-17-iodo-4,4,6,8,16-pentamethyl-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

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

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

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

There total 19 articles about (12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-17-iodo-4,4,6,8,16-pentamethyl-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: 100.0%

: 240816-00-6
(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-17-iodo-4,4,6,8,16-pentamethyl-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienal

: 240816-01-7
(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-17-iodo-4,4,6,8,16-pentamethyl-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; tert-butyl alcohol; at 25 ℃; for 0.666667h;
DOI:10.1016/S0968-0896(98)00153-9

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 240816-01-7
(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-17-iodo-4,4,6,8,16-pentamethyl-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / -20 - 0 °C

2: 84 percent / HF*pyr / pyridine; tetrahydrofuran / 3 h / 0 °C

3: 98 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 25 °C

4: 100 percent / 2-methyl-2-butene, NaH₂PO₄, NaClO₂ / 2-methyl-propan-2-ol; tetrahydrofuran / 0.67 h / 25 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; tert-butyl alcohol;
DOI:10.1016/S0968-0896(98)00153-9

Reference yield:

: 76-83-5
trityl chloride

: 240816-01-7
(12E,16E)-(3S,6R,7S,8S,15S)-3,7,15-Tris-(tert-butyl-dimethyl-silanyloxy)-17-iodo-4,4,6,8,16-pentamethyl-5-oxo-12-trityloxymethyl-heptadeca-12,16-dienoic acid

Guidance literature:: Multi-step reaction with 11 steps

1: 95 percent / 4-DMAP / dimethylformamide / 21 h / 80 °C

2: 95 percent / 9-BBN / tetrahydrofuran / 9 h / 0 °C

3: 97 percent / I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.75 h / 0 °C

4: 1.) LDA / 1.) THf, hexane, 0 deg C, 16 h, 2.) THf, hexane, -100 deg C to -20 deg C, 20 h

5: 89 percent / MMPP*6H₂O, phosphate buffer / tetrahydrofuran; methanol / 3 h / 0 °C

6: 88 percent / DIBAL / toluene / -78 °C

7: 1.) LDA / 1.) THF, hexane, -78 deg C, 1.5 h, -78 deg C to -40 deg C, 40 min, 2.) THF, hexane, -78 deg C, 1 h

8: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / -20 - 0 °C

9: 84 percent / HF*pyr / pyridine; tetrahydrofuran / 3 h / 0 °C

10: 98 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 25 °C

11: 100 percent / 2-methyl-2-butene, NaH₂PO₄, NaClO₂ / 2-methyl-propan-2-ol; tetrahydrofuran / 0.67 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; 2-methyl-but-2-ene; oxalyl dichloride; MMPP; iodine; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0968-0896(98)00153-9