(4aR,5aS,9R,10aS,11R,11aR,3'S)-11-(p-bromobenzoyloxy)-9-((E)-3',4'-di(p-bromobenzoyloxy)-1'-butenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-oxepino[2',3':5,6]pyrano[3,2-d]-1,3-dioxin

Base Information

Chemical Name:(4aR,5aS,9R,10aS,11R,11aR,3'S)-11-(p-bromobenzoyloxy)-9-((E)-3',4'-di(p-bromobenzoyloxy)-1'-butenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-oxepino[2',3':5,6]pyrano[3,2-d]-1,3-dioxin
CAS No.:173613-36-0
Molecular Formula:C₃₈H₃₅Br₃O₁₀
Molecular Weight:891.402
Hs Code.:

(4aR,5aS,9R,10aS,11R,11aR,3'S)-11-(p-bromobenzoyloxy)-9-((E)-3',4'-di(p-bromobenzoyloxy)-1'-butenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-oxepino[2',3':5,6]pyrano[3,2-d]-1,3-dioxin

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Chemical Property of (4aR,5aS,9R,10aS,11R,11aR,3'S)-11-(p-bromobenzoyloxy)-9-((E)-3',4'-di(p-bromobenzoyloxy)-1'-butenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-oxepino[2',3':5,6]pyrano[3,2-d]-1,3-dioxin

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Technology Process of (4aR,5aS,9R,10aS,11R,11aR,3'S)-11-(p-bromobenzoyloxy)-9-((E)-3',4'-di(p-bromobenzoyloxy)-1'-butenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-oxepino[2',3':5,6]pyrano[3,2-d]-1,3-dioxin

There total 12 articles about (4aR,5aS,9R,10aS,11R,11aR,3'S)-11-(p-bromobenzoyloxy)-9-((E)-3',4'-di(p-bromobenzoyloxy)-1'-butenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-oxepino[2',3':5,6]pyrano[3,2-d]-1,3-dioxin 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:

: 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-formyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

: 173613-36-0
(4aR,5aS,9R,10aS,11R,11aR,3'S)-11-(p-bromobenzoyloxy)-9-((E)-3',4'-di(p-bromobenzoyloxy)-1'-butenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-oxepino[2',3':5,6]pyrano[3,2-d]-1,3-dioxin

Guidance literature:: Multi-step reaction with 5 steps

1: benzene / 1.5 h / Ambient temperature

2: CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -60 °C

3: 93 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 89 percent / DDQ / CH₂Cl₂ / 3 h / Ambient temperature

5: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; sodium tetrahydroborate; cerium(III) chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; benzene;
DOI:10.1016/S0040-4020(97)00071-9

Reference yield:

: 173613-34-8
4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-hydroxymethyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

: 173613-36-0
(4aR,5aS,9R,10aS,11R,11aR,3'S)-11-(p-bromobenzoyloxy)-9-((E)-3',4'-di(p-bromobenzoyloxy)-1'-butenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-oxepino[2',3':5,6]pyrano[3,2-d]-1,3-dioxin

Guidance literature:: Multi-step reaction with 6 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / Ambient temperature

2: benzene / 1.5 h / Ambient temperature

3: CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -60 °C

4: 93 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 89 percent / DDQ / CH₂Cl₂ / 3 h / Ambient temperature

6: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; sodium tetrahydroborate; cerium(III) chloride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; benzene;
DOI:10.1016/S0040-4020(97)00071-9

Reference yield:

: 173613-32-6
4-Bromo-benzoic acid (4aR,5aS,8R,9S,10aS,11R,11aR)-8-hydroxy-2,2-dimethyl-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

: 173613-36-0
(4aR,5aS,9R,10aS,11R,11aR,3'S)-11-(p-bromobenzoyloxy)-9-((E)-3',4'-di(p-bromobenzoyloxy)-1'-butenyl)-4,4a,5a,6,9,10a,11,11a-octahydro-oxepino[2',3':5,6]pyrano[3,2-d]-1,3-dioxin

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -80 deg C, 15 min, 2.) 0 deg C, 4 h

2: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 20 h / Ambient temperature

3: 98 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temperature, 1.5 h

4: 64 percent / DBU / toluene / 58 h / 100 °C

5: 94 percent / n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

6: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / Ambient temperature

7: benzene / 1.5 h / Ambient temperature

8: CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -60 °C

9: 93 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / Ambient temperature

10: 89 percent / DDQ / CH₂Cl₂ / 3 h / Ambient temperature

11: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; Dess-Martin periodane; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;
DOI:10.1016/S0040-4020(97)00071-9