(S)-[(2R,3R)-3-(benzyloxy)pent-4-en-2-yl] 4-(tert-butyldimethylsilyloxy)hept-6-enoate

Base Information

Chemical Name:(S)-[(2R,3R)-3-(benzyloxy)pent-4-en-2-yl] 4-(tert-butyldimethylsilyloxy)hept-6-enoate
CAS No.:1292297-96-1
Molecular Formula:C₂₅H₄₀O₄Si
Molecular Weight:432.676
Hs Code.:

Synonyms:(S)-[(2R,3R)-3-(benzyloxy)pent-4-en-2-yl] 4-(tert-butyldimethylsilyloxy)hept-6-enoate

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Chemical Property of (S)-[(2R,3R)-3-(benzyloxy)pent-4-en-2-yl] 4-(tert-butyldimethylsilyloxy)hept-6-enoate

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Technology Process of (S)-[(2R,3R)-3-(benzyloxy)pent-4-en-2-yl] 4-(tert-butyldimethylsilyloxy)hept-6-enoate

There total 17 articles about (S)-[(2R,3R)-3-(benzyloxy)pent-4-en-2-yl] 4-(tert-butyldimethylsilyloxy)hept-6-enoate 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: 80.0%

: 1229358-27-3
(2R,3R)-3-(benzyloxy)pent-4-en-2-ol

: 4136-95-2
2,4,6-trichlorobenzoyl chloride

: 1292297-94-9
(S)-4-(tert-butyldimethylsilyloxy)hept-6-enoic acid

: 1292297-96-1
(S)-[(2R,3R)-3-(benzyloxy)pent-4-en-2-yl] 4-(tert-butyldimethylsilyloxy)hept-6-enoate

Guidance literature:: 2,4,6-trichlorobenzoyl chloride; (S)-4-(tert-butyldimethylsilyloxy)hept-6-enoic acid; With triethylamine; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

(2R,3R)-3-(benzyloxy)pent-4-en-2-ol; With dmap; In toluene; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1055/s-0030-1258389

Reference yield:

: 1026024-89-4
(S)-5-[(4-methoxybenzyl)oxy]pentane-1,2-diol

: 1292297-96-1
(S)-[(2R,3R)-3-(benzyloxy)pent-4-en-2-yl] 4-(tert-butyldimethylsilyloxy)hept-6-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: potassium carbonate / methanol / 0 - 20 °C / Inert atmosphere

3.1: copper(l) iodide / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 20 °C / Inert atmosphere

6.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; acetonitrile / 2 h / 20 °C / Inert atmosphere

7.1: triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7.2: 3 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(l) iodide; [bis(acetoxy)iodo]benzene; di(n-butyl)tin oxide; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 7.1: Yamaguchi esterification / 7.2: Yamaguchi esterification;
DOI:10.1055/s-0030-1258389

Reference yield:

: 1292297-91-6
(S)-7-(4-methoxybenzyloxy)hept-1-en-4-ol

: 1292297-96-1
(S)-[(2R,3R)-3-(benzyloxy)pent-4-en-2-yl] 4-(tert-butyldimethylsilyloxy)hept-6-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 20 °C / Inert atmosphere

3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; acetonitrile / 2 h / 20 °C / Inert atmosphere

4.1: triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

4.2: 3 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetonitrile; 4.1: Yamaguchi esterification / 4.2: Yamaguchi esterification;
DOI:10.1055/s-0030-1258389