(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

Base Information

Chemical Name:(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
CAS No.:262279-41-4
Molecular Formula:C₄₁H₄₈BrN₃O₈Si
Molecular Weight:818.837
Hs Code.:

Synonyms:(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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (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

There total 18 articles about (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 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: 92.0%

: 262279-40-3
(3S,8R,9S)-(E)-tert-butyl 3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-hydroxymethyl-2,4'-trisoxazole-4'-yl)-non-5-enoate

: 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

Guidance literature:: With 2,6-dimethylpyridine; carbon tetrabromide; triphenylphosphine; In N,N-dimethyl-formamide; for 0.5h;
DOI:10.1021/ja994003r

Reference yield:

: 14036-55-6
t-butyl vinylacetate

: 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

Guidance literature:: Multi-step reaction with 7 steps

1.1: 28.4 g / m-CPBA / CHCl₃ / 20 °C

2.1: 94 percent / AcOH; water / (R,R)-salen-Co / 12 h / 20 °C

3.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

3.2: imidazole / dimethylformamide / 20 °C

3.3: 100 percent / iodine / tetrahydrofuran / 0.5 h / 0 °C

4.1: 80 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylformamide / 20 °C

5.1: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 94 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

7.1: 92 percent / CBr₄; PPh₃; 2,6-lutidine / dimethylformamide / 0.5 h

With pyridine; 2,6-dimethylpyridine; chromium dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; nickel dichloride; (R,R)-Salen-Co; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; 5.1: Dess-Martin oxidation;
DOI:10.1021/ja002377a

Reference yield:

: 108100-50-1,111058-62-9,56936-16-4
(+/-)-tert-butyl 3,4-epoxybutanoate

: 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

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / AcOH; water / (R,R)-salen-Co / 12 h / 20 °C

2.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

2.2: imidazole / dimethylformamide / 20 °C

2.3: 100 percent / iodine / tetrahydrofuran / 0.5 h / 0 °C

3.1: 80 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylformamide / 20 °C

4.1: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 94 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

6.1: 92 percent / CBr₄; PPh₃; 2,6-lutidine / dimethylformamide / 0.5 h

With pyridine; 2,6-dimethylpyridine; chromium dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; acetic acid; triphenylphosphine; nickel dichloride; (R,R)-Salen-Co; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation;
DOI:10.1021/ja002377a