((E)-(2R,5S,7S,8R)-10-Benzenesulfonyl-5-benzyloxy-7-methoxy-2,8-dimethyl-dec-9-enyloxy)-tert-butyl-diphenyl-silane

Base Information

Chemical Name:((E)-(2R,5S,7S,8R)-10-Benzenesulfonyl-5-benzyloxy-7-methoxy-2,8-dimethyl-dec-9-enyloxy)-tert-butyl-diphenyl-silane
CAS No.:135663-90-0
Molecular Formula:C₄₂H₅₄O₅SSi
Molecular Weight:699.039
Hs Code.:

Synonyms:((E)-(2R,5S,7S,8R)-10-Benzenesulfonyl-5-benzyloxy-7-methoxy-2,8-dimethyl-dec-9-enyloxy)-tert-butyl-diphenyl-silane

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Chemical Property of ((E)-(2R,5S,7S,8R)-10-Benzenesulfonyl-5-benzyloxy-7-methoxy-2,8-dimethyl-dec-9-enyloxy)-tert-butyl-diphenyl-silane

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Technology Process of ((E)-(2R,5S,7S,8R)-10-Benzenesulfonyl-5-benzyloxy-7-methoxy-2,8-dimethyl-dec-9-enyloxy)-tert-butyl-diphenyl-silane

There total 27 articles about ((E)-(2R,5S,7S,8R)-10-Benzenesulfonyl-5-benzyloxy-7-methoxy-2,8-dimethyl-dec-9-enyloxy)-tert-butyl-diphenyl-silane 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

: 135663-90-0
((E)-(2R,5S,7S,8R)-10-Benzenesulfonyl-5-benzyloxy-7-methoxy-2,8-dimethyl-dec-9-enyloxy)-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 15 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

13: 2,6-di-tert-butylpyridine

14: Irradiation

15: MCBBA

With pyridine; 1H-imidazole; lead(IV) acetate; potassium fluoride; N-Bromosuccinimide; N-iodo-succinimide; 2,6-di-tert-butyl-pyridine; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; RhCl(PPh₃)3; In hexane; dichloromethane; water; 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

: 135663-90-0
((E)-(2R,5S,7S,8R)-10-Benzenesulfonyl-5-benzyloxy-7-methoxy-2,8-dimethyl-dec-9-enyloxy)-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 14 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

12: 2,6-di-tert-butylpyridine

13: Irradiation

14: MCBBA

With 1H-imidazole; lead(IV) acetate; potassium fluoride; N-Bromosuccinimide; N-iodo-succinimide; 2,6-di-tert-butyl-pyridine; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; RhCl(PPh₃)3; In hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo00020a027

Reference yield:

: 135663-45-5
Methanesulfonic acid (2R,3R,4S,5S,6S)-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-iodo-6-methoxy-tetrahydro-pyran-3-yl ester

: 135663-90-0
((E)-(2R,5S,7S,8R)-10-Benzenesulfonyl-5-benzyloxy-7-methoxy-2,8-dimethyl-dec-9-enyloxy)-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 13 steps

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

2: 74 percent / BF₃*OEt₂ / CH₂Cl₂ / 24 h / 23 °C

3: 72 percent / lead tetraacetate / benzene / 0.25 h

4: 62 percent / CH₂Cl₂ / 0.25 h / 0 °C

6: 83 percent / H₂ / RhCl(PPh₃)3 / benzene / 72 h / 23 °C / 760 Torr

7: 90 percent / DIBAH / hexane; toluene / 0.5 h / 0 °C

8: 100 percent / imidazole / dimethylformamide / 3 h / 23 °C

9: 89 percent / NBS / acetone; H₂O / 0.08 h / -20 °C

11: 2,6-di-tert-butylpyridine

12: Irradiation

13: MCBBA

With 1H-imidazole; lead(IV) acetate; potassium fluoride; N-Bromosuccinimide; 2,6-di-tert-butyl-pyridine; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; RhCl(PPh₃)3; In hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1021/jo00020a027