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

Base Information

Chemical Name: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
CAS No.:792919-87-0
Molecular Formula:C₃₆H₅₀O₇Si
Molecular Weight:622.874
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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: 90.0%

: 117968-51-1
methyl-1-(tert-butyldimethylsilyloxy)-4-butynoate

: 792919-86-9
(2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-3-ol

: 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

Guidance literature:: With trimethylphosphane; In dichloromethane; at 24 ℃; for 1h;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 100-39-0
benzyl bromide

: 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

Guidance literature:: Multi-step reaction with 3 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

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; trimethylphosphane; In tetrahydrofuran; 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

: 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

Guidance literature:: Multi-step reaction with 7 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

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