(3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide

Base Information

Chemical Name:(3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide
CAS No.:607403-20-3
Molecular Formula:C₂₃H₂₈N₂O₈S
Molecular Weight:492.55
Hs Code.:

Synonyms:(3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide

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Chemical Property of (3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide

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Technology Process of (3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide

There total 10 articles about (3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide 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: 85.0%

: 77-76-9
2,2-dimethoxy-propane

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

: 607403-20-3
(3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(03)00531-6

Reference yield:

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

: 607403-20-3
(3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide

Guidance literature:: Multi-step reaction with 9 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⁺

9.1: 85 percent / p-TsOH / dimethylformamide

With pyridine; Dowex-H⁺; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 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

: 607403-20-3
(3aS,4R,7S,7aR)-7-Hydroxy-5-(4-methoxy-benzenesulfonyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylic acid benzyloxy-amide

Guidance literature:: Multi-step reaction with 6 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⁺

6: 85 percent / p-TsOH / dimethylformamide

With Dowex-H⁺; hydrogen; sodium methylate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Mitsunobu reaction;
DOI:10.1016/S0960-894X(03)00531-6