(2R,3S,4R,5S)-3,4,5-trihydroxy-1-(4'-methoxybenzenesulfonyl)-piperidine-2-carboxylic acid benzyloxyamide

Base Information

Chemical Name:(2R,3S,4R,5S)-3,4,5-trihydroxy-1-(4'-methoxybenzenesulfonyl)-piperidine-2-carboxylic acid benzyloxyamide
CAS No.:607403-19-0
Molecular Formula:C₂₀H₂₄N₂O₈S
Molecular Weight:452.485
Hs Code.:

Synonyms:(2R,3S,4R,5S)-3,4,5-trihydroxy-1-(4'-methoxybenzenesulfonyl)-piperidine-2-carboxylic acid benzyloxyamide

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Chemical Property of (2R,3S,4R,5S)-3,4,5-trihydroxy-1-(4'-methoxybenzenesulfonyl)-piperidine-2-carboxylic acid benzyloxyamide

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Technology Process of (2R,3S,4R,5S)-3,4,5-trihydroxy-1-(4'-methoxybenzenesulfonyl)-piperidine-2-carboxylic acid benzyloxyamide

There total 9 articles about (2R,3S,4R,5S)-3,4,5-trihydroxy-1-(4'-methoxybenzenesulfonyl)-piperidine-2-carboxylic acid benzyloxyamide 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: 97.0%

: 607403-17-8
(3aS,6R,7S,7aS)-7-hydroxy-5-(4'-methoxybenzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid benzyloxyamide

: 607403-19-0
(2R,3S,4R,5S)-3,4,5-trihydroxy-1-(4'-methoxybenzenesulfonyl)-piperidine-2-carboxylic acid benzyloxyamide

Guidance literature:: With Dowex-H⁺;
DOI:10.1016/S0960-894X(03)00531-6

Reference yield:

: (4-methoxy-benzenesulfonylamino)-acetic acid benzyl ester

: 607403-19-0
(2R,3S,4R,5S)-3,4,5-trihydroxy-1-(4'-methoxybenzenesulfonyl)-piperidine-2-carboxylic acid benzyloxyamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: LDA

1.2: 65 percent / SnCl₂

2.1: pyridine

3.1: TBAF; AcOH / tetrahydrofuran

4.1: 87 percent / DEAD; Ph₃P / tetrahydrofuran

5.1: H₂ / Pd/C

6.1: 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide*HCl; 1-hydroxybenzotriazole

7.1: NaOMe / methanol

8.1: 97 percent / DOWEX-H⁺

With pyridine; Dowex-H⁺; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; 4.1: Mitsunobu reaction;
DOI:10.1016/S0960-894X(03)00531-6

Reference yield:

: 642089-78-9
(2R,3S,4'S,5'S)-3-acetoxy-3-[5'-hydroxymethyl-2',2'-dimethyl-[1,3]dioxolan-4'-yl]-2-(4-methoxybenzenesulfonylamino)-propionic acid benzyl ester

: 607403-19-0
(2R,3S,4R,5S)-3,4,5-trihydroxy-1-(4'-methoxybenzenesulfonyl)-piperidine-2-carboxylic acid benzyloxyamide

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / DEAD; Ph₃P / tetrahydrofuran

2: H₂ / Pd/C

3: 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide*HCl; 1-hydroxybenzotriazole

4: NaOMe / methanol

5: 97 percent / DOWEX-H⁺

With Dowex-H⁺; hydrogen; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1: Mitsunobu reaction;
DOI:10.1016/S0960-894X(03)00531-6