(S)-4-benzyloxy-3-(7-bromo-2-hydroxy-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester

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Chemical Name:(S)-4-benzyloxy-3-(7-bromo-2-hydroxy-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester
CAS No.:302964-56-3
Molecular Formula:C₃₆H₃₆BrNO₇
Molecular Weight:674.588
Hs Code.:

Synonyms:(S)-4-benzyloxy-3-(7-bromo-2-hydroxy-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester

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Chemical Property of (S)-4-benzyloxy-3-(7-bromo-2-hydroxy-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester

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Technology Process of (S)-4-benzyloxy-3-(7-bromo-2-hydroxy-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester

There total 9 articles about (S)-4-benzyloxy-3-(7-bromo-2-hydroxy-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl 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: 88.0%

: 302964-55-2
(S)-4-benzyloxy-3-(1-(3-bromo-2-hydroxyphenyl)prop-2-enyl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester

: 302964-56-3
(S)-4-benzyloxy-3-(7-bromo-2-hydroxy-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester

Guidance literature:: With osmium(VIII) oxide; potassium metaperiodate; In methanol; ethyl acetate;
DOI:10.1016/S0040-4039(00)01118-7

Reference yield:

: 16881-33-7
(S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate hydrate

: 302964-56-3
(S)-4-benzyloxy-3-(7-bromo-2-hydroxy-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: NaI; chloramine T / dimethylsulfoxide / 24 h

2: 13.9 g / n-Bu₄NI; K₂CO₃ / dimethylformamide / 22 h / 25 °C

3: 91 percent / LiCl / PdCl₂(PPh₃)2 / dimethylformamide / 22 h / 70 °C

4: 97 percent / PBr₃; pyridine / diethyl ether / 2 h / 20 °C

5: 74 percent / aq. NaOH; n-Bu₄NHSO₄ / benzene / 0.67 h / 25 °C

6: 50 percent / dimethylformamide / 11 h / Heating

7: 88 percent / aq. KIO₄; OsO₄ / ethyl acetate; methanol; diethyl ether / 8 h / 25 °C

With pyridine; sodium hydroxide; osmium(VIII) oxide; potassium metaperiodate; chloroamine-T; tetra(n-butyl)ammonium hydrogensulfate; phosphorus tribromide; tetra-(n-butyl)ammonium iodide; potassium carbonate; sodium iodide; lithium chloride; bis-triphenylphosphine-palladium(II) chloride; In methanol; diethyl ether; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene; 3: Stille coupling / 6: Claisen rearrangement;
DOI:10.1039/b510653b

Reference yield:

: 302964-51-8
(S)-4-benzyloxy-3-iodo-N-(benzyloxycarbonyl)tyrosine tert-butyl ester

: 302964-56-3
(S)-4-benzyloxy-3-(7-bromo-2-hydroxy-1,2-dihydrobenzo[b]furan-3-yl)-N-(benzyloxycarbonyl)tyrosine tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / LiCl / PdCl₂(PPh₃)2 / dimethylformamide / 22 h / 70 °C

2: 97 percent / PBr₃; pyridine / diethyl ether / 2 h / 20 °C

3: 74 percent / aq. NaOH; n-Bu₄NHSO₄ / benzene / 0.67 h / 25 °C

4: 50 percent / dimethylformamide / 11 h / Heating

5: 88 percent / aq. KIO₄; OsO₄ / ethyl acetate; methanol; diethyl ether / 8 h / 25 °C

With pyridine; sodium hydroxide; osmium(VIII) oxide; potassium metaperiodate; tetra(n-butyl)ammonium hydrogensulfate; phosphorus tribromide; lithium chloride; bis-triphenylphosphine-palladium(II) chloride; In methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; benzene; 1: Stille coupling / 4: Claisen rearrangement;
DOI:10.1039/b510653b