(S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester

Base Information

Chemical Name:(S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester
CAS No.:607403-12-3
Molecular Formula:C₂₉H₄₃NO₉SSi
Molecular Weight:609.813
Hs Code.:

(S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester

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Chemical Property of (S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester

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Technology Process of (S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester

There total 1 articles about (S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester 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: 65.0%

: 108817-97-6
(4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

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

: 607403-12-3
(S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester

Guidance literature:: (4-methoxy-benzenesulfonylamino)-acetic acid benzyl ester; With lithium diisopropyl amide;

With tin(ll) chloride;

(4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde;
DOI:10.1016/S0960-894X(03)00531-6

Reference yield:

: 607403-12-3
(S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-propionic acid benzyl ester

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

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine

2: TBAF; AcOH / tetrahydrofuran

3: 87 percent / DEAD; Ph₃P / tetrahydrofuran

4: H₂ / Pd/C

5: 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide*HCl; 1-hydroxybenzotriazole

6: NaOMe / methanol

7: 97 percent / DOWEX-H⁺

8: 96 percent / H₂ / Pd/C

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

Reference yield:

: 607403-12-3
(S)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-3-hydroxy-2-(4-methoxy-benzenesulfonylamino)-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 8 steps

1: pyridine

2: TBAF; AcOH / tetrahydrofuran

3: 87 percent / DEAD; Ph₃P / tetrahydrofuran

4: H₂ / Pd/C

5: 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide*HCl; 1-hydroxybenzotriazole

6: NaOMe / methanol

7: 97 percent / DOWEX-H⁺

8: 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; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 3: Mitsunobu reaction;
DOI:10.1016/S0960-894X(03)00531-6