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

Base Information

Chemical Name:(2E,2'S,3'R,5'Z,8'S,9'R)-3-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenol
CAS No.:792920-00-4
Molecular Formula:C₃₅H₅₀O₆Si
Molecular Weight:594.864
Hs Code.:

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

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

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

There total 9 articles about (2E,2'S,3'R,5'Z,8'S,9'R)-3-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenol 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: 99.0%

: 792919-87-0
methyl (2E,2'S,3'R,5'Z,8'S,9'R)-3-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenoate

: 792920-00-4
(2E,2'S,3'R,5'Z,8'S,9'R)-3-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.166667h;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 100-39-0
benzyl bromide

: 792920-00-4
(2E,2'S,3'R,5'Z,8'S,9'R)-3-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenol

Guidance literature:: Multi-step reaction with 4 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

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; 3: hetero-Michael addition;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 475641-59-9
(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

: 792920-00-4
(2E,2'S,3'R,5'Z,8'S,9'R)-3-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 24 percent / TFA; H₂O / tetrahydrofuran / 4 h / 0 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -20 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / 24 °C

3.2: tetrahydrofuran / 2.5 h / -78 °C

4.1: 113.5 mg / 1,2-ethanedithiol; NaHCL₃; Zn(OTf)2 / CH₂Cl₂ / 2.5 h / 0 °C

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

6.1: 135.8 mg / TBAF / tetrahydrofuran / 18 h / 25 °C

7.1: 90 percent / PMe₃ / CH₂Cl₂ / 1 h / 24 °C

8.1: 99 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; ethane-1,2-dithiol; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; 2.1: Swern oxidation / 3.2: Wittig reaction / 7.1: hetero-Michael addition;
DOI:10.1016/j.tet.2005.05.073