tert-Butyl-((R)-1-{(2R,5S,2'S)-5,2'-dimethyl-5'-[(4S,5S,6R)-2,2,5-trimethyl-6-((E)-(1R,5R,7R)-1,5,7-trimethyl-8-trityloxy-oct-2-enyl)-[1,3]dioxan-4-ylmethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethoxy)-dimethyl-silane

Base Information

Chemical Name:tert-Butyl-((R)-1-{(2R,5S,2'S)-5,2'-dimethyl-5'-[(4S,5S,6R)-2,2,5-trimethyl-6-((E)-(1R,5R,7R)-1,5,7-trimethyl-8-trityloxy-oct-2-enyl)-[1,3]dioxan-4-ylmethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethoxy)-dimethyl-silane
CAS No.:128329-47-5
Molecular Formula:C₅₆H₈₄O₆Si
Molecular Weight:881.365
Hs Code.:

tert-Butyl-((R)-1-{(2R,5S,2'S)-5,2'-dimethyl-5'-[(4S,5S,6R)-2,2,5-trimethyl-6-((E)-(1R,5R,7R)-1,5,7-trimethyl-8-trityloxy-oct-2-enyl)-[1,3]dioxan-4-ylmethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethoxy)-dimethyl-silane

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Chemical Property of tert-Butyl-((R)-1-{(2R,5S,2'S)-5,2'-dimethyl-5'-[(4S,5S,6R)-2,2,5-trimethyl-6-((E)-(1R,5R,7R)-1,5,7-trimethyl-8-trityloxy-oct-2-enyl)-[1,3]dioxan-4-ylmethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethoxy)-dimethyl-silane

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Technology Process of tert-Butyl-((R)-1-{(2R,5S,2'S)-5,2'-dimethyl-5'-[(4S,5S,6R)-2,2,5-trimethyl-6-((E)-(1R,5R,7R)-1,5,7-trimethyl-8-trityloxy-oct-2-enyl)-[1,3]dioxan-4-ylmethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethoxy)-dimethyl-silane

There total 42 articles about tert-Butyl-((R)-1-{(2R,5S,2'S)-5,2'-dimethyl-5'-[(4S,5S,6R)-2,2,5-trimethyl-6-((E)-(1R,5R,7R)-1,5,7-trimethyl-8-trityloxy-oct-2-enyl)-[1,3]dioxan-4-ylmethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethoxy)-dimethyl-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:

: C₆₄H₉₂O₁₀SSi

: 128329-47-5,128440-36-8
tert-Butyl-((R)-1-{(2R,5S,2'S)-5,2'-dimethyl-5'-[(4S,5S,6R)-2,2,5-trimethyl-6-((E)-(1R,5R,7R)-1,5,7-trimethyl-8-trityloxy-oct-2-enyl)-[1,3]dioxan-4-ylmethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethoxy)-dimethyl-silane

Guidance literature:: With sodium amalgam; In methanol; ethyl acetate; at -50 - -30 ℃; for 17h; Yield given;
DOI:10.1021/ja00169a041

Reference yield:

: 106820-50-2
2,3-dideoxy-3-C-methyl-5-O-tert-butyldiphenylsilyl-D-threo-pentono-1,4-lactone

: 128329-47-5,128440-36-8
tert-Butyl-((R)-1-{(2R,5S,2'S)-5,2'-dimethyl-5'-[(4S,5S,6R)-2,2,5-trimethyl-6-((E)-(1R,5R,7R)-1,5,7-trimethyl-8-trityloxy-oct-2-enyl)-[1,3]dioxan-4-ylmethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethoxy)-dimethyl-silane

Guidance literature:: Multi-step reaction with 24 steps

1: 78 percent / KHMDS, MoOPH / tetrahydrofuran / -78 - -30 °C

3: 94 percent / triethylamine, DMAP / CH₂Cl₂ / 6 h

4: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

5: 1.) n-Bu₄NF, 2.) sodium methoxide / 1.) THF, RT, 2.) 0.5 h

6: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 0.5 h, 2.) RT, overnight

7: ethyl((dimethylamino)propyl)carbodiimide hydrochloride (EDAC*HCl), DMAP / CH₂Cl₂ / 0.5 h / 0 °C

8: 30percent hydrogen peroxide / CH₂Cl₂ / 0.5 h / 0 °C

9: 97 percent / CuI, LiBr / diethyl ether / 1 h / -20 °C

10: 53 percent / KHMDS, MoOPH / tetrahydrofuran; toluene / -78 - -30 °C

11: lithium aluminum hydride / tetrahydrofuran / 4 h / Ambient temperature

12: pyridine / 1.) 0 deg C, 1 h, 2.) RT, 1 h

13: camphorsulfonic acid / various solvent(s) / 0.03 h

14: lithium aluminum hydride / tetrahydrofuran / 0.5 h / 0 °C

15: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

16: potassium carbonate / methanol / Ambient temperature

17: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, THF, -78 deg C, 15 min, 2.) -78 deg C , 1 h

18: 72 percent / 1 M tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h

19: 1.) mercury trifluoroacetate, 2.) sodium borohydride, 10percent aq. NaOH / 1.) THF, water, 0 deg C, 2 h, 2.) 0 deg C, 5 min

20: 87 percent / ammonia (liquid), sodium / tetrahydrofuran / 0.25 h / -33 °C

21: 90 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

22: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg C, 1 h

23: tetrahydrofuran; hexane / 90 h / Ambient temperature

24: sodium amalgam / methanol; ethyl acetate / 17 h / -50 - -30 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; sodium amalgam; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; MoO₅*pyridine*HMPA; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; sodium methylate; sodium hexamethyldisilazane; mercury(II) trifluoroacetate; sodium; potassium hexamethylsilazane; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/ja00169a041

Reference yield:

: 128329-22-6
(2R,3S)-<(tert-butyldiphenylsilyl)oxy>-2-methyl-1,3-butanediol

: 128329-47-5,128440-36-8
tert-Butyl-((R)-1-{(2R,5S,2'S)-5,2'-dimethyl-5'-[(4S,5S,6R)-2,2,5-trimethyl-6-((E)-(1R,5R,7R)-1,5,7-trimethyl-8-trityloxy-oct-2-enyl)-[1,3]dioxan-4-ylmethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethoxy)-dimethyl-silane

Guidance literature:: Multi-step reaction with 22 steps

1: 94 percent / triethylamine, DMAP / CH₂Cl₂ / 6 h

2: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.) n-Bu₄NF, 2.) sodium methoxide / 1.) THF, RT, 2.) 0.5 h

4: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 0.5 h, 2.) RT, overnight

5: ethyl((dimethylamino)propyl)carbodiimide hydrochloride (EDAC*HCl), DMAP / CH₂Cl₂ / 0.5 h / 0 °C

6: 30percent hydrogen peroxide / CH₂Cl₂ / 0.5 h / 0 °C

7: 97 percent / CuI, LiBr / diethyl ether / 1 h / -20 °C

8: 53 percent / KHMDS, MoOPH / tetrahydrofuran; toluene / -78 - -30 °C

9: lithium aluminum hydride / tetrahydrofuran / 4 h / Ambient temperature

10: pyridine / 1.) 0 deg C, 1 h, 2.) RT, 1 h

11: camphorsulfonic acid / various solvent(s) / 0.03 h

12: lithium aluminum hydride / tetrahydrofuran / 0.5 h / 0 °C

13: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

14: potassium carbonate / methanol / Ambient temperature

15: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, THF, -78 deg C, 15 min, 2.) -78 deg C , 1 h

16: 72 percent / 1 M tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h

17: 1.) mercury trifluoroacetate, 2.) sodium borohydride, 10percent aq. NaOH / 1.) THF, water, 0 deg C, 2 h, 2.) 0 deg C, 5 min

18: 87 percent / ammonia (liquid), sodium / tetrahydrofuran / 0.25 h / -33 °C

19: 90 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

20: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg C, 1 h

21: tetrahydrofuran; hexane / 90 h / Ambient temperature

22: sodium amalgam / methanol; ethyl acetate / 17 h / -50 - -30 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; sodium amalgam; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; MoO₅*pyridine*HMPA; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; sodium methylate; sodium hexamethyldisilazane; mercury(II) trifluoroacetate; sodium; potassium hexamethylsilazane; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/ja00169a041