(-)-(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-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-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-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one
• CAS No.: 502613-89-0
• Molecular Formula: C₃₃H₅₀O₆Si
• Molecular Weight: 570.842

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-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

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-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

Chemical Property:

Purity/Quality:

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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-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-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-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-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: 94.0%

triethylsilyl trifluoromethyl sulfonate (79271-56-0) + (+)-(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 (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-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one (502613-89-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1021/ol027575g 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,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one (502613-89-0)

Guidance literature:

Multi-step reaction with 14 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

14.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 20 °C

With 2,6-dimethylpyridine; 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

Reference yield:

(-)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylpropane-1,2-diol (502614-15-5) → (-)-(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-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one (502613-89-0)

Guidance literature:

Multi-step reaction with 13 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

13.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 20 °C

With 2,6-dimethylpyridine; 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

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

(+)-(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

(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:

(-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol

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