(2S,3R,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2,3-epoxypentanol

Base Information

Chemical Name:(2S,3R,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2,3-epoxypentanol
CAS No.:863222-43-9
Molecular Formula:C₃₆H₅₂O₇Si
Molecular Weight:624.89
Hs Code.:

(2S,3R,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2,3-epoxypentanol

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Chemical Property of (2S,3R,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2,3-epoxypentanol

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Technology Process of (2S,3R,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2,3-epoxypentanol

There total 14 articles about (2S,3R,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2,3-epoxypentanol 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:

: tert-Butyl-dimethyl-((Z)-(2R,4aR,6S,7R,11aS)-2-phenyl-6-vinyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-yloxy)-silane

: 863222-43-9
(2S,3R,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2,3-epoxypentanol

Guidance literature:: Multi-step reaction with 11 steps

1: 113.5 mg / 1,2-ethanedithiol; NaHCL₃; Zn(OTf)2 / CH₂Cl₂ / 2.5 h / 0 °C

2: NaH; TBAI / tetrahydrofuran / 15 h / 24 °C

3: 135.8 mg / TBAF / tetrahydrofuran / 18 h / 25 °C

4: 90 percent / PMe₃ / CH₂Cl₂ / 1 h / 24 °C

5: 99 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

6: 76 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 24 °C

7: 79 percent / Me₃Al / benzene; hexane / 1 h / 24 °C

8: 55 percent / Bu₃SnH; BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -18 °C

9: 100 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

10: 28.5 mg / DIBAH / CH₂Cl₂; hexane / 0.33 h / -78 °C

11: 100 percent / L-(+)-DET; Ti(O-iPr)4; TBHP / CH₂Cl₂; toluene / 26 h / -25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; trimethylaluminum; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; ethane-1,2-dithiol; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; toluene; benzene; 4: hetero-Michael addition / 11: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 863222-42-8
(2E,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-pentenal

: 863222-43-9
(2S,3R,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2,3-epoxypentanol

Guidance literature:: Multi-step reaction with 2 steps

1: 28.5 mg / DIBAH / CH₂Cl₂; hexane / 0.33 h / -78 °C

2: 100 percent / L-(+)-DET; Ti(O-iPr)4; TBHP / CH₂Cl₂; toluene / 26 h / -25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; diisobutylaluminium hydride; In hexane; dichloromethane; toluene; 2: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 100-39-0
benzyl bromide

: 863222-43-9
(2S,3R,2'S,3'R,5'Z,8'S,9'R)-4-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2,3-epoxypentanol

Guidance literature:: Multi-step reaction with 10 steps

1: NaH; TBAI / tetrahydrofuran / 15 h / 24 °C

2: 135.8 mg / TBAF / tetrahydrofuran / 18 h / 25 °C

3: 90 percent / PMe₃ / CH₂Cl₂ / 1 h / 24 °C

4: 99 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

5: 76 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 24 °C

6: 79 percent / Me₃Al / benzene; hexane / 1 h / 24 °C

7: 55 percent / Bu₃SnH; BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -18 °C

8: 100 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

9: 28.5 mg / DIBAH / CH₂Cl₂; hexane / 0.33 h / -78 °C

10: 100 percent / L-(+)-DET; Ti(O-iPr)4; TBHP / CH₂Cl₂; toluene / 26 h / -25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; trimethylaluminum; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; toluene; benzene; 3: hetero-Michael addition / 10: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1016/j.tet.2005.05.073