2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester

Base Information

Chemical Name:2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester
CAS No.:507277-19-2
Molecular Formula:C₃₈H₄₉NO₆S
Molecular Weight:647.876
Hs Code.:

Synonyms:2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester

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Chemical Property of 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester

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Technology Process of 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester

There total 5 articles about 2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl 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:

: 47375-34-8
Boc-Tyr(t-Bu)-OH

: 507277-19-2
2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: isobutylchloroformate; N-methylmorpholine / tetrahydrofuran / 0.33 h / -20 °C

1.2: 85 percent / tetrahydrofuran; diethyl ether / 0.5 h / -20 °C

2.1: 100 percent / PhCO₂Ag; NEt₃ / 1.25 h

3.1: 43 percent / DIBAL-H / toluene / 1 h / -78 °C

4.1: 46 percent / tetrahydrofuran / 1.5 h / -78 - -40 °C

5.1: Cl₂(PCy)3(IMesH₂)RuCHPh / CH₂Cl₂ / Heating

With 4-methyl-morpholine; silver benzoate; diisobutylaluminium hydride; triethylamine; isobutyl chloroformate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; toluene; 1.2: Arndt-Eistert homologation;
DOI:10.1021/ol027237f

Reference yield:

: 507276-78-0
3-tert-butoxycarbonylamino-4-(4-tert-butoxy-phenyl)-butyric acid methyl ester

: 507277-19-2
2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 43 percent / DIBAL-H / toluene / 1 h / -78 °C

2: 46 percent / tetrahydrofuran / 1.5 h / -78 - -40 °C

3: Cl₂(PCy)3(IMesH₂)RuCHPh / CH₂Cl₂ / Heating

With diisobutylaluminium hydride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ol027237f

Reference yield:

: 507276-76-8
[1-(4-tert-butoxybenzyl)-3-diazo-2-oxo-propyl]-carbamic acid tert-butyl ester

: 507277-19-2
2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,6-dihydroxy-non-4-enethioic acid S-benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / PhCO₂Ag; NEt₃ / 1.25 h

2: 43 percent / DIBAL-H / toluene / 1 h / -78 °C

3: 46 percent / tetrahydrofuran / 1.5 h / -78 - -40 °C

4: Cl₂(PCy)3(IMesH₂)RuCHPh / CH₂Cl₂ / Heating

With silver benzoate; diisobutylaluminium hydride; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ol027237f