(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

Base Information

Chemical Name:(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
CAS No.:792920-01-5
Molecular Formula:C₃₀H₃₈O₆
Molecular Weight:494.628
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 18 articles about (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 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: 68.0%

: 792919-92-7
(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)pent-1-en-3-ol

: 792920-01-5
(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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 11.5h;
DOI:10.1016/j.tetlet.2004.08.117 DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 100-39-0
benzyl bromide

: 792920-01-5
(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

Guidance literature:: Multi-step reaction with 13 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

11: I₂; PPh₃; imidazole / tetrahydrofuran / 0.58 h / 25 °C

12: 19.3 mg / Zn / ethanol / 2.5 h / 25 °C

13: 68 percent / TBAF / tetrahydrofuran / 11.5 h / 25 °C

With 1H-imidazole; 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; iodine; trimethylaluminum; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; zinc; trimethylphosphane; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; benzene; 3: hetero-Michael addition / 10: Katsuki-Sharpless asymmetric epoxidation;
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

: 792920-01-5
(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

Guidance literature:: Multi-step reaction with 17 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

10.1: 79 percent / Me₃Al / benzene; hexane / 1 h / 24 °C

11.1: 55 percent / Bu₃SnH; BF₃*Et₂O / CH₂Cl₂ / 0.25 h / -18 °C

12.1: 100 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

13.1: 28.5 mg / DIBAH / CH₂Cl₂; hexane / 0.33 h / -78 °C

14.1: 100 percent / L-(+)-DET; Ti(O-iPr)4; TBHP / CH₂Cl₂; toluene / 26 h / -25 °C

15.1: I₂; PPh₃; imidazole / tetrahydrofuran / 0.58 h / 25 °C

16.1: 19.3 mg / Zn / ethanol / 2.5 h / 25 °C

17.1: 68 percent / TBAF / tetrahydrofuran / 11.5 h / 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; iodine; trimethylaluminum; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; ethane-1,2-dithiol; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; zinc; trimethylphosphane; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; benzene; 2.1: Swern oxidation / 3.2: Wittig reaction / 7.1: hetero-Michael addition / 14.1: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1016/j.tet.2005.05.073