4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-[(E)-3-hydroxy-4-(4-methoxy-benzyloxy)-but-1-enyl]-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

Base Information

• Chemical Name: 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-[(E)-3-hydroxy-4-(4-methoxy-benzyloxy)-but-1-enyl]-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester
• CAS No.: 188050-74-0
• Molecular Formula: C₃₂H₃₇BrO₉
• Molecular Weight: 645.544

Synonyms:4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-[(E)-3-hydroxy-4-(4-methoxy-benzyloxy)-but-1-enyl]-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

Chemical Property of 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-[(E)-3-hydroxy-4-(4-methoxy-benzyloxy)-but-1-enyl]-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

Chemical Property:

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Safty Information:

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Technology Process of 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-[(E)-3-hydroxy-4-(4-methoxy-benzyloxy)-but-1-enyl]-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

There total 8 articles about 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-[(E)-3-hydroxy-4-(4-methoxy-benzyloxy)-but-1-enyl]-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester 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-[(E)-4-(4-methoxy-benzyloxy)-3-oxo-but-1-enyl]-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester → 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-[(E)-3-hydroxy-4-(4-methoxy-benzyloxy)-but-1-enyl]-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (188050-74-0)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -60 ℃; for 1h; Yield given;

DOI:10.1016/S0040-4020(97)00071-9

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 → 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-[(E)-3-hydroxy-4-(4-methoxy-benzyloxy)-but-1-enyl]-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (188050-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene / 1.5 h / Ambient temperature

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

With sodium tetrahydroborate; cerium(III) chloride; In methanol; benzene;

DOI:10.1016/S0040-4020(97)00071-9

Reference yield:

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 (173613-34-8) → 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-[(E)-3-hydroxy-4-(4-methoxy-benzyloxy)-but-1-enyl]-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (188050-74-0)

Guidance literature:

Multi-step reaction with 3 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

With sodium tetrahydroborate; cerium(III) chloride; Dess-Martin periodane; In methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4020(97)00071-9

upstream raw materials:

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

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

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

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

Downstream raw materials:

C₃₉H₄₀Br₂O₁₀

C₃₁H₃₂Br₂O₉

(4aR,5aS,9R,10aS,11R,11aR)-11-Benzyloxymethoxy-9-((E)-(S)-3,4-bis-benzyloxymethoxy-but-1-enyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

(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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