(Z)-(2R,3R,7R,8S)-2-Benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,7-dihydroxy-non-4-enoic acid

Base Information

Chemical Name:(Z)-(2R,3R,7R,8S)-2-Benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,7-dihydroxy-non-4-enoic acid
CAS No.:479496-01-0
Molecular Formula:C₃₁H₄₃NO₇
Molecular Weight:541.685
Hs Code.:

Synonyms:(Z)-(2R,3R,7R,8S)-2-Benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,7-dihydroxy-non-4-enoic acid

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Chemical Property of (Z)-(2R,3R,7R,8S)-2-Benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,7-dihydroxy-non-4-enoic acid

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Technology Process of (Z)-(2R,3R,7R,8S)-2-Benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,7-dihydroxy-non-4-enoic acid

There total 7 articles about (Z)-(2R,3R,7R,8S)-2-Benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,7-dihydroxy-non-4-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: 100.0%

: 479495-97-1
2-benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,7-dihydroxy-non-4-enethioic acid S-benzyl ester

: 479496-01-0
(Z)-(2R,3R,7R,8S)-2-Benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,7-dihydroxy-non-4-enoic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1021/ja027150p

Reference yield:

: 479496-23-6
2-benzyl-3-hydroxy-pent-4-enoic acid

: 479496-01-0
(Z)-(2R,3R,7R,8S)-2-Benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,7-dihydroxy-non-4-enoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / DCC; DMAP / CH₂Cl₂

2: 60 percent / pyridine

3: 89 percent / Cl₂(PCy₃)(IMesH₂)RuCHPh / toluene / 95 °C

4: 85 percent / HF; pyridine / tetrahydrofuran / 0.5 h / 0 °C

5: 100 percent / aq,LiOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; lithium hydroxide; hydrogen fluoride; dihydrogen peroxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja027150p

Reference yield:

: 3-Phenyl-propionic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

: 479496-01-0
(Z)-(2R,3R,7R,8S)-2-Benzyl-8-tert-butoxycarbonylamino-9-(4-tert-butoxy-phenyl)-3,7-dihydroxy-non-4-enoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: Cy₂BOTf; NEt₃ / CH₂Cl₂

1.2: aq. NaOH / tetrahydrofuran; methanol

2.1: 99 percent / DCC; DMAP / CH₂Cl₂

3.1: 60 percent / pyridine

4.1: 89 percent / Cl₂(PCy₃)(IMesH₂)RuCHPh / toluene / 95 °C

5.1: 85 percent / HF; pyridine / tetrahydrofuran / 0.5 h / 0 °C

6.1: 100 percent / aq,LiOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; lithium hydroxide; hydrogen fluoride; dihydrogen peroxide; triethylamine; dicyclohexyl-carbodiimide; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja027150p