(+)-(2R,4bS,9aS,9bR,11aS)-2-[1-(benzyloxy)-1-methylethyl]-5,6,6a,7,9,9a,9b,10,11,11a-decahydro-4b-(hydroperoxy)-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-3,9(4bH)-dione

Base Information

• Chemical Name: (+)-(2R,4bS,9aS,9bR,11aS)-2-[1-(benzyloxy)-1-methylethyl]-5,6,6a,7,9,9a,9b,10,11,11a-decahydro-4b-(hydroperoxy)-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-3,9(4bH)-dione
• CAS No.: 671792-37-3
• Molecular Formula: C₂₇H₃₄O₇
• Molecular Weight: 470.563

Synonyms:(+)-(2R,4bS,9aS,9bR,11aS)-2-[1-(benzyloxy)-1-methylethyl]-5,6,6a,7,9,9a,9b,10,11,11a-decahydro-4b-(hydroperoxy)-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-3,9(4bH)-dione

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

There total 22 articles about (+)-(2R,4bS,9aS,9bR,11aS)-2-[1-(benzyloxy)-1-methylethyl]-5,6,6a,7,9,9a,9b,10,11,11a-decahydro-4b-(hydroperoxy)-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-3,9(4bH)-dione 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:

3-(1-benzyloxy-1-methyl-ethyl)-8,14-dimethyl-6,7,8,11,12,13,14,17-octahydro-1H,5H-4,16-dioxa-cyclopenta[a]phenanthrene-2,15-dione → (+)-(2R,4bS,9aS,9bR,11aS)-2-[1-(benzyloxy)-1-methylethyl]-5,6,6a,7,9,9a,9b,10,11,11a-decahydro-4b-(hydroperoxy)-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-3,9(4bH)-dione (671792-37-3)

Guidance literature:

With air; silica gel; In acetone; at 20 ℃; for 16h;

DOI:10.1002/hlca.200390328

Reference yield:

(2R,3R)-1,2-O-isopropylidene-4-methyl-4-pentene-1,2,3-triol (139629-93-9) → (+)-(2R,4bS,9aS,9bR,11aS)-2-[1-(benzyloxy)-1-methylethyl]-5,6,6a,7,9,9a,9b,10,11,11a-decahydro-4b-(hydroperoxy)-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-3,9(4bH)-dione (671792-37-3)

Guidance literature:

Multi-step reaction with 15 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

14: DMP / CH₂Cl₂ / 1 h / 20 °C

15: 2.5 mg / air; silica gel / acetone / 16 h / 20 °C

With triethylsilane; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; N-iodo-succinimide; perchloric acid; air; trifluorormethanesulfonic acid; phthalic acid dimethyl ester; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; sodium acetate; acetic anhydride; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; acetic acid; (+)-10-camphorsulfonic acid; triphenylphosphine; N-tosylimidazole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; acetonitrile; benzene; 14: Dess-Martin oxidation;

DOI:10.1002/hlca.200390328

Reference yield:

(+)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-hydroxypropan-2-one (83657-30-1) → (+)-(2R,4bS,9aS,9bR,11aS)-2-[1-(benzyloxy)-1-methylethyl]-5,6,6a,7,9,9a,9b,10,11,11a-decahydro-4b-(hydroperoxy)-9a,9b-dimethyl-2H-[2]benzofuro[5,4-f][1]benzopyran-3,9(4bH)-dione (671792-37-3)

Guidance literature:

Multi-step reaction with 14 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

13: DMP / CH₂Cl₂ / 1 h / 20 °C

14: 2.5 mg / air; silica gel / acetone / 16 h / 20 °C

With triethylsilane; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; N-iodo-succinimide; perchloric acid; air; trifluorormethanesulfonic acid; phthalic acid dimethyl ester; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; sodium acetate; acetic anhydride; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; (+)-10-camphorsulfonic acid; N-tosylimidazole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; acetonitrile; benzene; 13: Dess-Martin oxidation;

DOI:10.1002/hlca.200390328

upstream raw materials:

(2R,3R)-1,2-O-isopropylidene-4-methyl-4-pentene-1,2,3-triol

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

C₂₂H₄₀O₃Si

(+)-(1R,9aS,9bS)-3,3a,4,5,8,9,9a,9b-octahydro-1-methoxy-9a,9b-dimethylnaphtho[1,2-c]furan-7(1H)-one

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