(2S, 3S)-2-azido-3-butanoic acid

Base Information

Chemical Name:(2S, 3S)-2-azido-3-butanoic acid
CAS No.:156721-26-5
Molecular Formula:C₂₁H₂₂N₄O₄S
Molecular Weight:426.496
Hs Code.:

(2S, 3S)-2-azido-3-<N-(2-mesitylenesulfonyl)-3-indolyl>butanoic acid

Synonyms:(2S, 3S)-2-azido-3-butanoic acid

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S, 3S)-2-azido-3-butanoic acid

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Technology Process of (2S, 3S)-2-azido-3-butanoic acid

There total 7 articles about (2S, 3S)-2-azido-3-butanoic 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: 72.0%

: 156769-33-4
(3(2S, 3S), 4R)-3-<2-azido-3-(N-(2-mesitylenesulfonyl)-3-indolyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone

: 156721-26-5
(2S, 3S)-2-azido-3-butanoic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 2h;
DOI:10.1016/S0040-4020(01)86957-X

Reference yield:

: 773-64-8
2-mesitylenesulphonyl chloride

: 156721-26-5
(2S, 3S)-2-azido-3-butanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / 1.6M butyllithium / tetrahydrofuran; hexane / 1.) -78 deg C - 0 deg C, 55 min, 2.) 0 deg C, 1 h, then RT, 2 h

2: triethylamine / tetrahydrofuran / -78 deg C - 0 deg C, 1 h

3: 1.6M nBuLi in hexane / tetrahydrofuran / -78 - 21 °C

4: 1.) CuBr-Me₂S, methyl sulfide, 2.) N-bromosuccinimide / 1.) THF, ether, 0 deg C, 2 h, then RT, 0.5 h, 2.) THF, -78 deg C, 2, h, then 0 deg C, 0.5 h

5: 78 percent / tetramethylguanidinium azide / acetonitrile / 120 h / Ambient temperature

6: 72 percent / LiOH*H₂O, 30percent H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

With lithium hydroxide; N-Bromosuccinimide; n-butyllithium; dimethylsulfide; dihydrogen peroxide; triethylamine; tetramethylguanidinum azide; In tetrahydrofuran; hexane; water; acetonitrile;
DOI:10.1016/S0040-4020(01)86957-X

Reference yield:

: 156721-17-4
(2-mesitylenesulfonyl)indole-3-acrylic acid

: 156721-26-5
(2S, 3S)-2-azido-3-butanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: triethylamine / tetrahydrofuran / -78 deg C - 0 deg C, 1 h

2: 1.6M nBuLi in hexane / tetrahydrofuran / -78 - 21 °C

3: 1.) CuBr-Me₂S, methyl sulfide, 2.) N-bromosuccinimide / 1.) THF, ether, 0 deg C, 2 h, then RT, 0.5 h, 2.) THF, -78 deg C, 2, h, then 0 deg C, 0.5 h

4: 78 percent / tetramethylguanidinium azide / acetonitrile / 120 h / Ambient temperature

5: 72 percent / LiOH*H₂O, 30percent H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

With lithium hydroxide; N-Bromosuccinimide; n-butyllithium; dimethylsulfide; dihydrogen peroxide; triethylamine; tetramethylguanidinum azide; In tetrahydrofuran; water; acetonitrile;
DOI:10.1016/S0040-4020(01)86957-X