(2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic acid

Base Information

Chemical Name:(2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic acid
CAS No.:1026641-14-4
Molecular Formula:C₃₃H₃₉NO₇
Molecular Weight:561.675
Hs Code.:

Synonyms:(2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic acid

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Chemical Property of (2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic acid

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Technology Process of (2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic acid

There total 12 articles about (2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic 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:

: 794525-86-3
tert-butyl (S)-(1-((2R,4R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzyl)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate

: 1026641-14-4
(2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic acid

Guidance literature:: With lithium hydroxide; In water; N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/jo0486948

Reference yield:

: 90-90-4
(4-bromophenyl)(phenyl)methanone

: 1026641-14-4
(2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / p-TsOH / benzene / 44 h / Heating

2.1: 95 percent / n-BuLi / tetrahydrofuran / -78 °C

3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / 0.5 h / -78 °C

3.3: 80 percent / Ac₂O; Et₃N / 1 h / 120 °C

4.1: 90 percent / H₂ / PtO₂ / ethyl acetate / 2 h / 20 °C

5.1: LiOH / dimethylformamide; H₂O / 20 °C

With lithium hydroxide; n-butyllithium; hydrogen; toluene-4-sulfonic acid; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo0486948

Reference yield:

: 51987-73-6
(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

: 1026641-14-4
(2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

2.1: 7.8 g / NaBH₄ / toluene; ethanol / 8 h / -78 - 0 °C

3.1: 89 percent / KOH / ethanol / 2 h / 20 °C

4.1: 90 percent / EtONa / ethanol / 20 °C

5.1: LiOH / dimethylformamide; H₂O / 6 h / 50 °C

6.1: toluene / 5 h / Heating

7.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

7.2: tetrahydrofuran / 0.5 h / -78 °C

7.3: 80 percent / Ac₂O; Et₃N / 1 h / 120 °C

8.1: 90 percent / H₂ / PtO₂ / ethyl acetate / 2 h / 20 °C

9.1: LiOH / dimethylformamide; H₂O / 20 °C

With potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; hydrogen; sodium ethanolate; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0486948