2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester
CAS No.:179945-08-5
Molecular Formula:C₅₄H₈₄O₇SSi
Molecular Weight:905.408
Hs Code.:

2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester

Synonyms:2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester

There total 30 articles about 2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester 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: 86.0%

: 179945-07-4
2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-9,15-dimethoxy-4,6,10,13-tetramethyl-16-trityloxy-hexadec-10-enyl ester

: 179945-08-5
2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester

: 2,2-Dimethyl-propionic acid (E)-(4S,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-oxo-16-trityloxy-hexadec-10-enyl ester

Guidance literature:: With acetic anhydride; acetic acid; dimethyl sulfoxide; 1.) 23 deg C, 2 h, 2.) 40 deg C, 5.5 h;
DOI:10.1021/jo9606113

Reference yield:

: 157430-98-3
(3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol

: 179945-08-5
2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: 99 percent / pyridine / 1.5 h / 0 °C

2: 99 percent / hydrogen / Pd on carbon / ethanol / 3.5 h / 23 °C

3: 91 percent / trubutylphosphine / dimethylformamide / 12 h / 23 °C

4: 100 percent / imidazole / dimethylformamide / 1.4 h / 23 °C

5: 100 percent / NaHCO₃, m-chloroperoxybenzoic acid / CH₂Cl₂ / 1.5 h / 23 °C

6: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, 23 deg C, 1.5 h

7: 316 mg / Na₂HPO₄, sodium amalgam / methanol / 2 h / 0 °C

8: 98 percent / NaHCO₃, hydrogen / Pd on carbon / ethanol / 2.5 h / 23 °C

9: 91 percent / pyridine, Dess-Martin periodinane / CH₂Cl₂ / 0.7 h / 23 °C

10: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -78 deg C, 1 h

11: 1.53 g / pyridine, Dess-Martin periodinane / CH₂Cl₂ / 0.7 h / 23 °C

12: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 2 h

13: 27 mg / Na₂HPO₄, sodium amalgam / methanol / 2.3 h / 0 °C

14: 43 percent / pyridine, phosphoryl trichloride / 24 h / 0 °C

15: 97 percent / acetic acid / tetrahydrofuran; H₂O / 6.6 h / 23 °C

16: 86 percent / acetic acid, acetic anhydride / 1.) 23 deg C, 2 h, 2.) 40 deg C, 5.5 h

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; sodium amalgam; copper(l) iodide; n-butyllithium; tributylphosphine; hydrogen; acetic anhydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo9606113

Reference yield:

: 179944-96-8
2,2-Dimethyl-propionic acid (3R,4R,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-7-phenylsulfanyl-heptyl ester

: 179945-08-5
2,2-Dimethyl-propionic acid (E)-(3R,4R,5R,6R,9S,13R,15R)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,10,13-tetramethyl-3-methylsulfanylmethoxy-16-trityloxy-hexadec-10-enyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 100 percent / imidazole / dimethylformamide / 1.4 h / 23 °C

2: 100 percent / NaHCO₃, m-chloroperoxybenzoic acid / CH₂Cl₂ / 1.5 h / 23 °C

3: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, 23 deg C, 1.5 h

4: 316 mg / Na₂HPO₄, sodium amalgam / methanol / 2 h / 0 °C

5: 98 percent / NaHCO₃, hydrogen / Pd on carbon / ethanol / 2.5 h / 23 °C

6: 91 percent / pyridine, Dess-Martin periodinane / CH₂Cl₂ / 0.7 h / 23 °C

7: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -78 deg C, 1 h

8: 1.53 g / pyridine, Dess-Martin periodinane / CH₂Cl₂ / 0.7 h / 23 °C

9: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 2 h

10: 27 mg / Na₂HPO₄, sodium amalgam / methanol / 2.3 h / 0 °C

11: 43 percent / pyridine, phosphoryl trichloride / 24 h / 0 °C

12: 97 percent / acetic acid / tetrahydrofuran; H₂O / 6.6 h / 23 °C

13: 86 percent / acetic acid, acetic anhydride / 1.) 23 deg C, 2 h, 2.) 40 deg C, 5.5 h

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; sodium amalgam; copper(l) iodide; n-butyllithium; hydrogen; acetic anhydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo9606113