(3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one

Base Information

Chemical Name:(3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one
CAS No.:615249-03-1
Molecular Formula:C₃₅H₅₁BrO₇Si
Molecular Weight:691.775
Hs Code.:

(3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one

Synonyms:(3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one

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Chemical Property of (3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one

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Technology Process of (3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one

There total 20 articles about (3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-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: 57.0%

: 615249-05-3
(1S,4S,5R)-2-Methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-ene

: 615249-04-2
(3aR,5R,6aS,8S,10aR)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one

: 615249-03-1
(3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one

: 615249-19-9
(3aS,5S,6aR,8R,10aS)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one

Guidance literature:: With bromine; N,N-dimethyl-aniline; In dichloromethane; at -78 - 0 ℃; for 12h;
DOI:10.1002/anie.200351744

Reference yield:

: 154278-40-7
(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate

: 615249-03-1
(3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / p-TsOH / methanol / 3 h / 25 °C

2: 57 percent / TMSOTf; iPr₂NEt / CH₂Cl₂ / 16 h / -20 - 25 °C

3: 57 percent / Br₂; N,N-dimethylaniline / CH₂Cl₂ / 12 h / -78 - 0 °C

With trimethylsilyl trifluoromethanesulfonate; bromine; toluene-4-sulfonic acid; N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;
DOI:10.1002/anie.200351744

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 615249-03-1
(3aR,5R,6aS,8S,10aR)-5-[(1S,2R,3R,4R,5R)-3-Bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-8-(tert-butyl-dimethyl-silanyloxy)-4-methylene-octahydro-2-oxa-cyclopenta[d]naphthalen-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 25 °C

2: 97 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 3 h / 25 °C

3: 78 percent / tetrahydrofuran / 12 h / 25 °C

4: 50 percent / SeO₂; t-BuOOH / CH₂Cl₂ / 6 h / 25 °C

5: 57 percent / Br₂; N,N-dimethylaniline / CH₂Cl₂ / 12 h / -78 - 0 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; selenium(IV) oxide; bromine; sodium hydrogencarbonate; Dess-Martin periodane; N,N-dimethyl-aniline; In tetrahydrofuran; dichloromethane; 2: Dess-martin oxidation / 3: Wittig reaction;
DOI:10.1002/anie.200351744