(2R,3R,4S)-3-(benzyloxy)-4-(tert-butyloxycarbonylamino)tetrahydrofuran-2-carboxylic acid

Base Information

Chemical Name:(2R,3R,4S)-3-(benzyloxy)-4-(tert-butyloxycarbonylamino)tetrahydrofuran-2-carboxylic acid
CAS No.:1198162-53-6
Molecular Formula:C₁₇H₂₃NO₆
Molecular Weight:337.373
Hs Code.:

Synonyms:(2R,3R,4S)-3-(benzyloxy)-4-(tert-butyloxycarbonylamino)tetrahydrofuran-2-carboxylic acid

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Chemical Property of (2R,3R,4S)-3-(benzyloxy)-4-(tert-butyloxycarbonylamino)tetrahydrofuran-2-carboxylic acid

Chemical Property:

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Technology Process of (2R,3R,4S)-3-(benzyloxy)-4-(tert-butyloxycarbonylamino)tetrahydrofuran-2-carboxylic acid

There total 7 articles about (2R,3R,4S)-3-(benzyloxy)-4-(tert-butyloxycarbonylamino)tetrahydrofuran-2-carboxylic 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: 94.0%

: 1198162-54-7
(2R,3R,4S)-methyl 3-(benzyloxy)-4-(tert-butoxycarbonylamino)-tetrahydrofuran-2-carboxylate

: 1198162-53-6
(2R,3R,4S)-3-(benzyloxy)-4-(tert-butyloxycarbonylamino)tetrahydrofuran-2-carboxylic acid

Guidance literature:: (2R,3R,4S)-methyl 3-(benzyloxy)-4-(tert-butoxycarbonylamino)-tetrahydrofuran-2-carboxylate; With lithium hydroxide monohydrate; In methanol; water; at 20 ℃; for 4h;

With hydrogenchloride; In methanol; water; pH=3;
DOI:10.1002/ejoc.201201565

Reference yield:

: 89860-19-5
(1R,2R,5R)-2-(dimethoxymethyl)-3,6-dioxabicyclo[3.1.0]hexane

: 1198162-53-6
(2R,3R,4S)-3-(benzyloxy)-4-(tert-butyloxycarbonylamino)tetrahydrofuran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium azide; ammonium chloride / water; ethanol / 24 h / Reflux

2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 20 °C

2.2: 3 h

3.1: trifluoroacetic acid; water / 2 h / 20 °C

4.1: N-Bromosuccinimide; potassium carbonate / acetonitrile / 24 h / 20 °C / Darkness

5.1: triphenylphosphine / tetrahydrofuran / 3 h

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C

7.1: lithium hydroxide monohydrate / methanol; water / 4 h / 20 °C

7.2: pH 3

With N-Bromosuccinimide; sodium azide; lithium hydroxide monohydrate; water; sodium hydride; potassium carbonate; ammonium chloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile; mineral oil;
DOI:10.1002/ejoc.201201565

Reference yield:

: 1198162-57-0
(2R,3R,4S)-methyl 4-azido-3-(benzyloxy)tetrahydrofuran-2-carboxylate

: 1198162-53-6
(2R,3R,4S)-3-(benzyloxy)-4-(tert-butyloxycarbonylamino)tetrahydrofuran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: triphenylphosphine / tetrahydrofuran / 3 h

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C

3.1: lithium hydroxide monohydrate / methanol; water / 4 h / 20 °C

3.2: pH 3

With lithium hydroxide monohydrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1002/ejoc.201201565