(+)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-9-one

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Chemical Name:(+)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-9-one
CAS No.:671792-36-2
Molecular Formula:C₂₇H₃₆O₅
Molecular Weight:440.58
Hs Code.:

Synonyms:(+)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-9-one

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Chemical Property of (+)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-9-one

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Technology Process of (+)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-9-one

There total 21 articles about (+)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-9-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: 81.0%

: 502613-94-7
(-)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-9-oxo-2H-[2]benzofuro[5,4-f][1]benzopyran-3-yl benzenecarboxylate

: 671792-36-2
(+)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-9-one

Guidance literature:: With potassium hydroxide; In methanol; water; for 6h; Heating;
DOI:10.1002/hlca.200390328

Reference yield:

: 139629-93-9
(2R,3R)-1,2-O-isopropylidene-4-methyl-4-pentene-1,2,3-triol

: 671792-36-2
(+)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-9-one

Guidance literature:: Multi-step reaction with 13 steps

1: 91 percent / O₃; PPh₃ / CH₂Cl₂ / 1.5 h / -78 °C

2: 90 percent / tetrahydrofuran; diethyl ether / 1 h / 20 °C

3: 58 percent / AcOH; Ac₂O / 38 h / 20 °C

4: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

5: 90 percent / (+)-camphorsulfonic acid / methanol; H₂O / 2.5 h / 65 °C

6: 91 percent / NaH; 1-tosyl-1H-imidazole / tetrahydrofuran / -78 - 0 °C / 2.2 Torr

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

8: DMAP / CH₂Cl₂ / 18 h / 20 °C

9: 615 mg / AcONa; AcOH / benzene / 45 h / 65 °C

10: 70 percent / aq. HClO₄ / acetonitrile / 1.25 h / 55 °C

11: 91 percent / N-iodosuccinimide; tetrabutylammonium iodide / CH₂Cl₂ / 1 h / 0 - 20 °C

12: 81 percent / Et₃SiH; TfOH / acetonitrile; CH₂Cl₂ / 1 h / -50 - -20 °C

13: 81 percent / KOH / methanol; H₂O / 6 h / Heating

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; ozone; acetic acid; (+)-10-camphorsulfonic acid; triphenylphosphine; N-tosylimidazole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 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

: 671792-36-2
(+)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-9-one

Guidance literature:: Multi-step reaction with 12 steps

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

2: 58 percent / AcOH; Ac₂O / 38 h / 20 °C

3: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

4: 90 percent / (+)-camphorsulfonic acid / methanol; H₂O / 2.5 h / 65 °C

5: 91 percent / NaH; 1-tosyl-1H-imidazole / tetrahydrofuran / -78 - 0 °C / 2.2 Torr

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

7: DMAP / CH₂Cl₂ / 18 h / 20 °C

8: 615 mg / AcONa; AcOH / benzene / 45 h / 65 °C

9: 70 percent / aq. HClO₄ / acetonitrile / 1.25 h / 55 °C

10: 91 percent / N-iodosuccinimide; tetrabutylammonium iodide / CH₂Cl₂ / 1 h / 0 - 20 °C

11: 81 percent / Et₃SiH; TfOH / acetonitrile; CH₂Cl₂ / 1 h / -50 - -20 °C

12: 81 percent / KOH / methanol; H₂O / 6 h / Heating

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; acetic acid; (+)-10-camphorsulfonic acid; N-tosylimidazole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; benzene;
DOI:10.1002/hlca.200390328