(5E,7E,9E)-(2R,4S,11S,13S,16R)-13-Benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trien-1-ol

Base Information

Chemical Name:(5E,7E,9E)-(2R,4S,11S,13S,16R)-13-Benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trien-1-ol
CAS No.:135663-82-0
Molecular Formula:C₄₅H₆₄O₄Si
Molecular Weight:697.086
Hs Code.:

(5E,7E,9E)-(2R,4S,11S,13S,16R)-13-Benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trien-1-ol

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Chemical Property of (5E,7E,9E)-(2R,4S,11S,13S,16R)-13-Benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trien-1-ol

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Technology Process of (5E,7E,9E)-(2R,4S,11S,13S,16R)-13-Benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trien-1-ol

There total 47 articles about (5E,7E,9E)-(2R,4S,11S,13S,16R)-13-Benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trien-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:

: 126461-69-6
1,5-anhydro-3-O-benzyl-6-O-tert-butyldimetylsilyl-2-deoxy-D-arabino-hex-1-enopyranose

: 135663-82-0,135758-75-7
(5E,7E,9E)-(2R,4S,11S,13S,16R)-13-Benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trien-1-ol

Guidance literature:: Multi-step reaction with 18 steps

1: 99 percent / pyridine / 12 h / 23 °C

2: 88 percent / N-iodosuccinimide / acetonitrile / 12 h / 23 °C

3: 1) tributyltin hydride, AIBN, 2) satd.aq.KF / 1) benzene, reflux, 5 h, 2) 12 h

4: 74 percent / BF₃*OEt₂ / CH₂Cl₂ / 24 h / 23 °C

5: 72 percent / lead tetraacetate / benzene / 0.25 h

6: 62 percent / CH₂Cl₂ / 0.25 h / 0 °C

8: 83 percent / H₂ / RhCl(PPh₃)3 / benzene / 72 h / 23 °C / 760 Torr

9: 90 percent / DIBAH / hexane; toluene / 0.5 h / 0 °C

10: 100 percent / imidazole / dimethylformamide / 3 h / 23 °C

11: 89 percent / NBS / acetone; H₂O / 0.08 h / -20 °C

12: CrCl₂, NiCl₂ / dimethylsulfoxide / 24 h / 23 °C

13: 100 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 18 h / Ambient temperature

14: 1) n-BuLi / 1) THF, hexane, -78 deg C, 20 min, 2) THF, -78 deg C, 30 min

15: Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 23 °C

16: 66 percent / N-chlorosuccinimide, AgNO₃ / acetonitrile; H₂O / 0.25 h / 23 °C

17: NaBH₄ / CH₂Cl₂; ethanol / 0.5 h / 0 °C

18: 5percent sodium amalgam, KH₂PO₄ / tetrahydrofuran; methanol / 1 h / -20 °C

With pyridine; 1H-imidazole; chromium dichloride; lead(IV) acetate; dmap; potassium fluoride; sodium tetrahydroborate; potassium dihydrogenphosphate; sodium amalgam; N-chloro-succinimide; N-Bromosuccinimide; N-iodo-succinimide; n-butyllithium; 2,6-di-tert-butyl-pyridine; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; silver nitrate; triethylamine; nickel dichloride; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo00020a027

Reference yield:

: 135663-48-8
(E)-(4R,5R)-5-Benzyloxy-6-[1,3]dithian-2-yl-4-methanesulfonyloxy-hex-2-enoic acid ethyl ester

: 135663-82-0,135758-75-7
(5E,7E,9E)-(2R,4S,11S,13S,16R)-13-Benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trien-1-ol

Guidance literature:: Multi-step reaction with 12 steps

2: 83 percent / H₂ / RhCl(PPh₃)3 / benzene / 72 h / 23 °C / 760 Torr

3: 90 percent / DIBAH / hexane; toluene / 0.5 h / 0 °C

4: 100 percent / imidazole / dimethylformamide / 3 h / 23 °C

5: 89 percent / NBS / acetone; H₂O / 0.08 h / -20 °C

6: CrCl₂, NiCl₂ / dimethylsulfoxide / 24 h / 23 °C

7: 100 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 18 h / Ambient temperature

8: 1) n-BuLi / 1) THF, hexane, -78 deg C, 20 min, 2) THF, -78 deg C, 30 min

9: Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 23 °C

10: 66 percent / N-chlorosuccinimide, AgNO₃ / acetonitrile; H₂O / 0.25 h / 23 °C

11: NaBH₄ / CH₂Cl₂; ethanol / 0.5 h / 0 °C

12: 5percent sodium amalgam, KH₂PO₄ / tetrahydrofuran; methanol / 1 h / -20 °C

With 1H-imidazole; chromium dichloride; dmap; sodium tetrahydroborate; potassium dihydrogenphosphate; sodium amalgam; N-chloro-succinimide; N-Bromosuccinimide; n-butyllithium; 2,6-di-tert-butyl-pyridine; hydrogen; diisobutylaluminium hydride; silver nitrate; triethylamine; nickel dichloride; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo00020a027

Reference yield:

: 135663-44-4
Methanesulfonic acid (2R,3S,4R)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester

: 135663-82-0,135758-75-7
(5E,7E,9E)-(2R,4S,11S,13S,16R)-13-Benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trien-1-ol

Guidance literature:: Multi-step reaction with 17 steps

1: 88 percent / N-iodosuccinimide / acetonitrile / 12 h / 23 °C

2: 1) tributyltin hydride, AIBN, 2) satd.aq.KF / 1) benzene, reflux, 5 h, 2) 12 h

3: 74 percent / BF₃*OEt₂ / CH₂Cl₂ / 24 h / 23 °C

4: 72 percent / lead tetraacetate / benzene / 0.25 h

5: 62 percent / CH₂Cl₂ / 0.25 h / 0 °C

7: 83 percent / H₂ / RhCl(PPh₃)3 / benzene / 72 h / 23 °C / 760 Torr

8: 90 percent / DIBAH / hexane; toluene / 0.5 h / 0 °C

9: 100 percent / imidazole / dimethylformamide / 3 h / 23 °C

10: 89 percent / NBS / acetone; H₂O / 0.08 h / -20 °C

11: CrCl₂, NiCl₂ / dimethylsulfoxide / 24 h / 23 °C

12: 100 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 18 h / Ambient temperature

13: 1) n-BuLi / 1) THF, hexane, -78 deg C, 20 min, 2) THF, -78 deg C, 30 min

14: Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 23 °C

15: 66 percent / N-chlorosuccinimide, AgNO₃ / acetonitrile; H₂O / 0.25 h / 23 °C

16: NaBH₄ / CH₂Cl₂; ethanol / 0.5 h / 0 °C

17: 5percent sodium amalgam, KH₂PO₄ / tetrahydrofuran; methanol / 1 h / -20 °C

With 1H-imidazole; chromium dichloride; lead(IV) acetate; dmap; potassium fluoride; sodium tetrahydroborate; potassium dihydrogenphosphate; sodium amalgam; N-chloro-succinimide; N-Bromosuccinimide; N-iodo-succinimide; n-butyllithium; 2,6-di-tert-butyl-pyridine; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; silver nitrate; triethylamine; nickel dichloride; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo00020a027