(E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-16-((E)-2-iodo-1-methyl-vinyl)-5,5,7,9-tetramethyl-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione

Base Information

• Chemical Name: (E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-16-((E)-2-iodo-1-methyl-vinyl)-5,5,7,9-tetramethyl-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione
• CAS No.: 240816-03-9
• Molecular Formula: C₅₄H₇₉IO₆Si₂
• Molecular Weight: 1007.29

Synonyms:

Chemical Property of (E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-16-((E)-2-iodo-1-methyl-vinyl)-5,5,7,9-tetramethyl-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-16-((E)-2-iodo-1-methyl-vinyl)-5,5,7,9-tetramethyl-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione

There total 20 articles about (E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-16-((E)-2-iodo-1-methyl-vinyl)-5,5,7,9-tetramethyl-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione 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:

t-butyldimethylsiyl triflate (69739-34-0) → (E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-16-((E)-2-iodo-1-methyl-vinyl)-5,5,7,9-tetramethyl-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione (240816-03-9)

Guidance literature:

Multi-step reaction with 6 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

5: 95 percent / TBAF / tetrahydrofuran / 19 h / 25 °C

6: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) 4-DMAP / 1.) THF, 0 deg C, 1.5 h, 2.) THF, 75 deg C, 0.5 h

With 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0968-0896(98)00153-9

Reference yield:

trityl chloride (76-83-5) → (E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-16-((E)-2-iodo-1-methyl-vinyl)-5,5,7,9-tetramethyl-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione (240816-03-9)

Guidance literature:

Multi-step reaction with 13 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

12: 95 percent / TBAF / tetrahydrofuran / 19 h / 25 °C

13: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) 4-DMAP / 1.) THF, 0 deg C, 1.5 h, 2.) THF, 75 deg C, 0.5 h

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; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; 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

Reference yield:

(3S,1E)-1-iodo-2-methylhexa-1,5-dien-3-ol (204513-22-4) → (E)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-16-((E)-2-iodo-1-methyl-vinyl)-5,5,7,9-tetramethyl-13-trityloxymethyl-oxacyclohexadec-13-ene-2,6-dione (240816-03-9)

Guidance literature:

Multi-step reaction with 18 steps

1: 84 percent / imidazole / dimethylformamide / 7 h / 0 - 25 °C

2: 89 percent / OsO₄, NMO / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 13 h / 25 °C

3: 92 percent / NaIO₄ / methanol; H₂O / 0.5 h / 25 °C

4: 98 percent / benzene / 1.5 h / Heating

5: 100 percent / DIBAL / tetrahydrofuran; CH₂Cl₂ / 1.33 h / -78 °C

6: 95 percent / 4-DMAP / dimethylformamide / 21 h / 80 °C

7: 95 percent / 9-BBN / tetrahydrofuran / 9 h / 0 °C

8: 97 percent / I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.75 h / 0 °C

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

10: 89 percent / MMPP*6H₂O, phosphate buffer / tetrahydrofuran; methanol / 3 h / 0 °C

11: 88 percent / DIBAL / toluene / -78 °C

12: 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

13: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / -20 - 0 °C

14: 84 percent / HF*pyr / pyridine; tetrahydrofuran / 3 h / 0 °C

15: 98 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 25 °C

16: 100 percent / 2-methyl-2-butene, NaH₂PO₄, NaClO₂ / 2-methyl-propan-2-ol; tetrahydrofuran / 0.67 h / 25 °C

17: 95 percent / TBAF / tetrahydrofuran / 19 h / 25 °C

18: 1.) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2.) 4-DMAP / 1.) THF, 0 deg C, 1.5 h, 2.) THF, 75 deg C, 0.5 h

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; phosphate buffer; 2-methyl-but-2-ene; oxalyl dichloride; MMPP; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1016/S0968-0896(98)00153-9

upstream raw materials:

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

t-butyldimethylsiyl triflate

trityl chloride

(3S,1E)-1-iodo-2-methylhexa-1,5-dien-3-ol

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