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

Base Information

• Chemical Name: (+)-(2S,3R,9aS,9bS,11aS)-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-2-(1-hydroxy-1-methylethyl)-9a,9b-dimethyl-9-oxo-2H-[2]benzofuro[5,4-f][1]benzopyran-3-yl benzenecarboxylate
• CAS No.: 671792-34-0
• Molecular Formula: C₂₇H₃₄O₆
• Molecular Weight: 454.563

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 21 articles about (+)-(2S,3R,9aS,9bS,11aS)-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-2-(1-hydroxy-1-methylethyl)-9a,9b-dimethyl-9-oxo-2H-[2]benzofuro[5,4-f][1]benzopyran-3-yl benzenecarboxylate 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: 95.0%

(-)-(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 (502613-94-7) → (+)-(2S,3R,9aS,9bS,11aS)-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-2-(1-hydroxy-1-methylethyl)-9a,9b-dimethyl-9-oxo-2H-[2]benzofuro[5,4-f][1]benzopyran-3-yl benzenecarboxylate (671792-34-0)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 3.5h;

DOI:10.1002/hlca.200390328

Reference yield:

(2R,3R)-1,2-O-isopropylidene-4-methyl-4-pentene-1,2,3-triol (139629-93-9) → (+)-(2S,3R,9aS,9bS,11aS)-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-2-(1-hydroxy-1-methylethyl)-9a,9b-dimethyl-9-oxo-2H-[2]benzofuro[5,4-f][1]benzopyran-3-yl benzenecarboxylate (671792-34-0)

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: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H₂O / CH₂Cl₂ / 3.5 h / 20 °C

With triethylsilane; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-iodo-succinimide; perchloric acid; trifluorormethanesulfonic acid; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; water; sodium acetate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; acetic acid; (+)-10-camphorsulfonic acid; triphenylphosphine; N-tosylimidazole; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; benzene;

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) → (+)-(2S,3R,9aS,9bS,11aS)-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-2-(1-hydroxy-1-methylethyl)-9a,9b-dimethyl-9-oxo-2H-[2]benzofuro[5,4-f][1]benzopyran-3-yl benzenecarboxylate (671792-34-0)

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: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H₂O / CH₂Cl₂ / 3.5 h / 20 °C

With triethylsilane; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-iodo-succinimide; perchloric acid; trifluorormethanesulfonic acid; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; water; sodium acetate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; (+)-10-camphorsulfonic acid; N-tosylimidazole; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; benzene;

DOI:10.1002/hlca.200390328

upstream raw materials:

(-)-(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

benzoyl chloride

(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

Downstream raw materials:

2-[2-amino-5-(3-methyl-but-2-enyl)-phenyl]-1-[8-hydroxymethyl-6a,7-dimethyl-3-(1-methyl-1-triethylsilanyloxy-ethyl)-2-triethylsilanyloxy-2,3,4a,5,6,6a,7,8,9,10-decahydro-1H-benzo[f]chromen-7-yl]-ethanone

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