(+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

Base Information

Chemical Name:(+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one
CAS No.:502613-96-9
Molecular Formula:C₂₇H₃₆O₆
Molecular Weight:456.579
Hs Code.:

(+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

Synonyms:(+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

Suppliers and Price of (+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

There total 29 articles about (+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one 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: 91.0%

: 502613-95-8
(-)-(2S,3R,4aR,5aS,10aS,10bRS,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-10a,10b-dimethyl-10-oxo-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-3-yl benzenecarboxylate

: 502613-96-9
(+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

Guidance literature:: (-)-(2S,3R,4aR,5aS,10aS,10bRS,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-10a,10b-dimethyl-10-oxo-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-3-yl benzenecarboxylate; With potassium hydroxide; In methanol; water; for 42h; Heating;

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 0.333333h;
DOI:10.1002/hlca.200390328

Reference yield:

: 502614-15-5
(-)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylpropane-1,2-diol

: 502613-96-9
(+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: 58 percent / AcOH; Ac₂O / 38 h / 20 °C

2.1: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

3.1: 90 percent / (+)-camphorsulfonic acid / methanol; H₂O / 2.5 h / 65 °C

4.1: 91 percent / NaH; 1-tosyl-1H-imidazole / tetrahydrofuran / -78 - 0 °C / 2.2 Torr

5.1: LiNEt₂; DMPU; chiral octahydronaphthalene dimethylhydrazone / tetrahydrofuran; hexane / 17 h / -40 - 65 °C

6.1: DMAP / CH₂Cl₂ / 18 h / 20 °C

7.1: 615 mg / AcONa; AcOH / benzene / 45 h / 65 °C

8.1: 70 percent / aq. HClO₄ / acetonitrile / 1.25 h / 55 °C

9.1: 91 percent / N-iodosuccinimide; tetrabutylammonium iodide / CH₂Cl₂ / 1 h / 0 - 20 °C

10.1: 81 percent / Et₃SiH; TfOH / acetonitrile; CH₂Cl₂ / 1 h / -50 - -20 °C

11.1: 77 percent / m-CPBA; NaHCO₃ / toluene / 48 h / 20 °C

12.1: KOH / methanol; H₂O / 42 h / Heating

12.2: 91 percent / DMAP; EDCI / CH₂Cl₂ / 0.33 h / 20 °C

With triethylsilane; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; N-iodo-succinimide; perchloric acid; trifluorormethanesulfonic acid; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; sodium acetate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; acetic acid; (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; N-tosylimidazole; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1002/hlca.200390328

Reference yield:

: 83657-30-1
(+)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-hydroxypropan-2-one

: 502613-96-9
(+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: 90 percent / tetrahydrofuran; diethyl ether / 1 h / 20 °C

2.1: 58 percent / AcOH; Ac₂O / 38 h / 20 °C

3.1: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

4.1: 90 percent / (+)-camphorsulfonic acid / methanol; H₂O / 2.5 h / 65 °C

5.1: 91 percent / NaH; 1-tosyl-1H-imidazole / tetrahydrofuran / -78 - 0 °C / 2.2 Torr

6.1: LiNEt₂; DMPU; chiral octahydronaphthalene dimethylhydrazone / tetrahydrofuran; hexane / 17 h / -40 - 65 °C

7.1: DMAP / CH₂Cl₂ / 18 h / 20 °C

8.1: 615 mg / AcONa; AcOH / benzene / 45 h / 65 °C

9.1: 70 percent / aq. HClO₄ / acetonitrile / 1.25 h / 55 °C

10.1: 91 percent / N-iodosuccinimide; tetrabutylammonium iodide / CH₂Cl₂ / 1 h / 0 - 20 °C

11.1: 81 percent / Et₃SiH; TfOH / acetonitrile; CH₂Cl₂ / 1 h / -50 - -20 °C

12.1: 77 percent / m-CPBA; NaHCO₃ / toluene / 48 h / 20 °C

13.1: KOH / methanol; H₂O / 42 h / Heating

13.2: 91 percent / DMAP; EDCI / CH₂Cl₂ / 0.33 h / 20 °C

With triethylsilane; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; N-iodo-succinimide; perchloric acid; trifluorormethanesulfonic acid; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; sodium acetate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; acetic acid; (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; N-tosylimidazole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1002/hlca.200390328