4-benzyl 1-tert-butyl (2S,3R)-2-allyl-3-({benzyl[(benzyloxy)carbonyl]amino}methyl)butanedioate

Base Information

Chemical Name:4-benzyl 1-tert-butyl (2S,3R)-2-allyl-3-({benzyl[(benzyloxy)carbonyl]amino}methyl)butanedioate
CAS No.:252919-23-6
Molecular Formula:C₃₄H₃₉NO₆
Molecular Weight:557.687
Hs Code.:

Synonyms:4-benzyl 1-tert-butyl (2S,3R)-2-allyl-3-({benzyl[(benzyloxy)carbonyl]amino}methyl)butanedioate

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Chemical Property of 4-benzyl 1-tert-butyl (2S,3R)-2-allyl-3-({benzyl[(benzyloxy)carbonyl]amino}methyl)butanedioate

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Technology Process of 4-benzyl 1-tert-butyl (2S,3R)-2-allyl-3-({benzyl[(benzyloxy)carbonyl]amino}methyl)butanedioate

There total 9 articles about 4-benzyl 1-tert-butyl (2S,3R)-2-allyl-3-({benzyl[(benzyloxy)carbonyl]amino}methyl)butanedioate 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: 87.0%

: 100-39-0
benzyl bromide

: 252919-12-3
(2R,3S)-2-({benzyl[(benzyloxy)carbonyl]amino}methyl)-3-(tert-butoxycarbonyl)-5-hexenoic acid

: 252919-23-6
4-benzyl 1-tert-butyl (2S,3R)-2-allyl-3-({benzyl[(benzyloxy)carbonyl]amino}methyl)butanedioate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 60 ℃; for 2h;
DOI:10.1021/jo016086b

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 252919-23-6
4-benzyl 1-tert-butyl (2S,3R)-2-allyl-3-({benzyl[(benzyloxy)carbonyl]amino}methyl)butanedioate

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 75 percent / tetrahydrofuran / 5 h / -30 °C

2.1: 90 percent / 30percent H₂O₂; aq. LiOH / tetrahydrofuran; H₂O / 2 h / 0 °C

3.1: LDA / tetrahydrofuran / 1 h / -78 °C

3.2: 80 percent / tetrahydrofuran / 5 h / -30 °C

4.1: 87 percent / DBU / benzene / 2 h / 60 °C

With lithium hydroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; water; benzene;
DOI:10.1021/jo016086b

Reference yield:

: 2304-94-1
3-(benzyloxycarbonylamino)propanoic acid

: 252919-23-6
4-benzyl 1-tert-butyl (2S,3R)-2-allyl-3-({benzyl[(benzyloxy)carbonyl]amino}methyl)butanedioate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / NaH / tetrahydrofuran; dimethylformamide / 20 °C

2.1: Et₃N / tetrahydrofuran / 1 h / -30 °C

3.1: 55.4 g / LiCl / tetrahydrofuran / 20 °C

4.1: LDA / tetrahydrofuran / 1 h / -78 °C

4.2: 75 percent / tetrahydrofuran / 5 h / -30 °C

5.1: 90 percent / 30percent H₂O₂; aq. LiOH / tetrahydrofuran; H₂O / 2 h / 0 °C

6.1: LDA / tetrahydrofuran / 1 h / -78 °C

6.2: 80 percent / tetrahydrofuran / 5 h / -30 °C

7.1: 87 percent / DBU / benzene / 2 h / 60 °C

With lithium hydroxide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo016086b