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
• Mol file: 792919-87-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

methyl-1-(tert-butyldimethylsilyloxy)-4-butynoate (117968-51-1) + (2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-3-ol (792919-86-9) → 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 (792919-87-0)

Guidance literature:

With trimethylphosphane; In dichloromethane; at 24 ℃; for 1h;

DOI:10.1016/j.tet.2005.05.073

Reference yield:

benzyl bromide (100-39-0) → 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 (792919-87-0)

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:

(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 (475641-59-9) → 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 (792919-87-0)

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

upstream raw materials:

methyl-1-(tert-butyldimethylsilyloxy)-4-butynoate

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

benzyl bromide

(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

Downstream raw materials:

(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

(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

(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

(3R,2'S,3'R,5'Z,8'S,9'R)-2-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}pent-4-en-1,3-diol