(5E,7Z,9E)-(2R,4S,11S,13S,16R)-8-Benzenesulfonyl-13-benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trienal

Base Information

Chemical Name:(5E,7Z,9E)-(2R,4S,11S,13S,16R)-8-Benzenesulfonyl-13-benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trienal
CAS No.:135663-85-3
Molecular Formula:C₅₁H₆₆O₆SSi
Molecular Weight:835.233
Hs Code.:

(5E,7Z,9E)-(2R,4S,11S,13S,16R)-8-Benzenesulfonyl-13-benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trienal

Synonyms:(5E,7Z,9E)-(2R,4S,11S,13S,16R)-8-Benzenesulfonyl-13-benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trienal

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Chemical Property of (5E,7Z,9E)-(2R,4S,11S,13S,16R)-8-Benzenesulfonyl-13-benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trienal

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Technology Process of (5E,7Z,9E)-(2R,4S,11S,13S,16R)-8-Benzenesulfonyl-13-benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trienal

There total 47 articles about (5E,7Z,9E)-(2R,4S,11S,13S,16R)-8-Benzenesulfonyl-13-benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trienal 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: 66.0%

: 135663-84-2
((8E,10Z,12E)-(2R,5S,7S,14S,16R)-10-Benzenesulfonyl-5-benzyloxy-16-[1,3]dithian-2-yl-7-methoxy-2,8,14-trimethyl-heptadeca-8,10,12-trienyloxy)-tert-butyl-diphenyl-silane

: 135663-85-3
(5E,7Z,9E)-(2R,4S,11S,13S,16R)-8-Benzenesulfonyl-13-benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trienal

Guidance literature:: With N-chloro-succinimide; silver nitrate; In water; acetonitrile; at 23 ℃; for 0.333333h;
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

: 135663-85-3
(5E,7Z,9E)-(2R,4S,11S,13S,16R)-8-Benzenesulfonyl-13-benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trienal

Guidance literature:: Multi-step reaction with 16 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: 89 percent / DBU / tetrahydrofuran / 1 h / 23 °C

16: 66 percent / N-chlorosuccinimide, AgNO₃ / acetonitrile; H₂O / 0.33 h / 23 °C

With 1H-imidazole; chromium dichloride; lead(IV) acetate; dmap; potassium fluoride; 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; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; nickel dichloride; RhCl(PPh₃)3; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo00020a027

Reference yield:

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

: 135663-85-3
(5E,7Z,9E)-(2R,4S,11S,13S,16R)-8-Benzenesulfonyl-13-benzyloxy-17-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-2,4,10,16-tetramethyl-heptadeca-5,7,9-trienal

Guidance literature:: Multi-step reaction with 17 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: 89 percent / DBU / tetrahydrofuran / 1 h / 23 °C

17: 66 percent / N-chlorosuccinimide, AgNO₃ / acetonitrile; H₂O / 0.33 h / 23 °C

With pyridine; 1H-imidazole; chromium dichloride; lead(IV) acetate; dmap; potassium fluoride; 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; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; nickel dichloride; RhCl(PPh₃)3; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo00020a027