(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-butenal

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-butenal
CAS No.:792919-88-1
Molecular Formula:C₃₅H₄₈O₆Si
Molecular Weight:592.848
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-butenal

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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-butenal

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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-butenal

There total 10 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-butenal 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: 76.0%

: 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

: 792919-88-1
(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-butenal

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; at 24 ℃; for 1.5h;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 100-39-0
benzyl bromide

: 792919-88-1
(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-butenal

Guidance literature:: Multi-step reaction with 5 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

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; 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

: 792919-88-1
(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-butenal

Guidance literature:: Multi-step reaction with 9 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

9.1: 76 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 24 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; 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