(3S,8R,9S)-(E)-3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoic acid

Base Information

Chemical Name:(3S,8R,9S)-(E)-3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoic acid
CAS No.:262279-24-3
Molecular Formula:C₃₇H₄₀BrN₃O₈Si
Molecular Weight:762.729
Hs Code.:

Synonyms:(3S,8R,9S)-(E)-3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoic acid

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Chemical Property of (3S,8R,9S)-(E)-3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoic acid

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Technology Process of (3S,8R,9S)-(E)-3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoic acid

There total 16 articles about (3S,8R,9S)-(E)-3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoic acid 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:

: 262279-41-4
(3S,8R,9S)-(E)-tert-butyl 3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoate

: 262279-24-3
(3S,8R,9S)-(E)-3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1021/ja994003r

Reference yield:

: 194232-63-8
2''-(tert-Butyl-diphenyl-silanyloxymethyl)-[2,4';2',4'']teroxazole-4-carbaldehyde

: 262279-24-3
(3S,8R,9S)-(E)-3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 65 percent / TiCl₄ / CH₂Cl₂ / 24 h / -78 - 20 °C

2: 93 percent / silver(I) oxide / 10 h / Heating

3: OsO₄; trimethylamine N-oxide dihydrate; t-BuOH / tetrahydrofuran; H₂O; toluene / 4 h / 20 °C

4: 773 mg / Pb(OAc)4; K₂CO₃ / diethyl ether / 0.25 h / 0 °C

5: 80 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylformamide / 20 °C

6: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

7: 94 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

8: 92 percent / CBr₄; PPh₃; 2,6-lutidine / dimethylformamide / 0.5 h

9: TFA / CH₂Cl₂ / 3 h / 0 °C

With pyridine; 2,6-dimethylpyridine; chromium dichloride; lead(IV) acetate; osmium(VIII) oxide; carbon tetrabromide; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; titanium tetrachloride; potassium carbonate; Dess-Martin periodane; triphenylphosphine; trifluoroacetic acid; nickel dichloride; silver(l) oxide; tert-butyl alcohol; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 6: Dess-Martin oxidation;
DOI:10.1021/ja002377a

Reference yield:

: 262279-31-2
(5S,6S)-(E)-methyl 6-methoxy-5-methyl-6-(2-tert-butyldiphenylsiloxymethyl-2,4'-trisoxazole-4'-yl)-hex-3-enoate

: 262279-24-3
(3S,8R,9S)-(E)-3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: OsO₄; trimethylamine N-oxide dihydrate; t-BuOH / tetrahydrofuran; H₂O; toluene / 4 h / 20 °C

2: 773 mg / Pb(OAc)4; K₂CO₃ / diethyl ether / 0.25 h / 0 °C

3: 80 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylformamide / 20 °C

4: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

5: 94 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

6: 92 percent / CBr₄; PPh₃; 2,6-lutidine / dimethylformamide / 0.5 h

7: TFA / CH₂Cl₂ / 3 h / 0 °C

With pyridine; 2,6-dimethylpyridine; chromium dichloride; lead(IV) acetate; osmium(VIII) oxide; carbon tetrabromide; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; potassium carbonate; Dess-Martin periodane; triphenylphosphine; trifluoroacetic acid; nickel dichloride; tert-butyl alcohol; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4: Dess-Martin oxidation;
DOI:10.1021/ja002377a