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

Base Information

Chemical Name:(2R,3S)-2-({benzyl[(benzyloxy)carbonyl]amino}methyl)-3-(tert-butoxycarbonyl)-5-hexenoic acid
CAS No.:252919-12-3
Molecular Formula:C₂₇H₃₃NO₆
Molecular Weight:467.562
Hs Code.:

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

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Chemical Property of (2R,3S)-2-({benzyl[(benzyloxy)carbonyl]amino}methyl)-3-(tert-butoxycarbonyl)-5-hexenoic acid

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Technology Process of (2R,3S)-2-({benzyl[(benzyloxy)carbonyl]amino}methyl)-3-(tert-butoxycarbonyl)-5-hexenoic acid

There total 8 articles about (2R,3S)-2-({benzyl[(benzyloxy)carbonyl]amino}methyl)-3-(tert-butoxycarbonyl)-5-hexenoic 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: 80.0%

: 556-56-9
allyl iodid

: 252919-11-2
(2R)-2-({benzyl[(benzyloxy)carbonyl]amino}methyl)-4-tert-butoxy-4-oxobutanoate

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

Guidance literature:: (2R)-2-({benzyl[(benzyloxy)carbonyl]amino}methyl)-4-tert-butoxy-4-oxobutanoate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

allyl iodid; In tetrahydrofuran; at -30 ℃; for 5h; Further stages.;
DOI:10.1021/jo016086b

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

With lithium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; water;
DOI:10.1021/jo016086b

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With lithium hydroxide; sodium hydride; triethylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1021/jo016086b