(2R)-4-[(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yloxy]-4-oxobutan-2-yl (4R,5S,E)-5-(acryloyloxy)-4-(tert-butyldimethylsilyloxy)hex-2-enoate

Base Information

Chemical Name:(2R)-4-[(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yloxy]-4-oxobutan-2-yl (4R,5S,E)-5-(acryloyloxy)-4-(tert-butyldimethylsilyloxy)hex-2-enoate
CAS No.:1379680-83-7
Molecular Formula:C₃₂H₄₈O₉Si
Molecular Weight:604.813
Hs Code.:

Synonyms:(2R)-4-[(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yloxy]-4-oxobutan-2-yl (4R,5S,E)-5-(acryloyloxy)-4-(tert-butyldimethylsilyloxy)hex-2-enoate

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Chemical Property of (2R)-4-[(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yloxy]-4-oxobutan-2-yl (4R,5S,E)-5-(acryloyloxy)-4-(tert-butyldimethylsilyloxy)hex-2-enoate

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Technology Process of (2R)-4-[(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yloxy]-4-oxobutan-2-yl (4R,5S,E)-5-(acryloyloxy)-4-(tert-butyldimethylsilyloxy)hex-2-enoate

There total 17 articles about (2R)-4-[(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yloxy]-4-oxobutan-2-yl (4R,5S,E)-5-(acryloyloxy)-4-(tert-butyldimethylsilyloxy)hex-2-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:

: 1379680-85-9
(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yl (3R)-3-hydroxybutanoate

: C₂₂H₂₇Cl₃O₆Si

: 1379680-83-7
(2R)-4-[(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yloxy]-4-oxobutan-2-yl (4R,5S,E)-5-(acryloyloxy)-4-(tert-butyldimethylsilyloxy)hex-2-enoate

Guidance literature:: With dmap; In toluene; at 0 - 20 ℃; for 6h; Inert atmosphere;
DOI:10.1002/ejoc.201101603

Reference yield:

: 1379680-91-7
(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yl (3R)-3-(tert-butyldimethylsilyloxy)butanoate

: 1379680-83-7
(2R)-4-[(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yloxy]-4-oxobutan-2-yl (4R,5S,E)-5-(acryloyloxy)-4-(tert-butyldimethylsilyloxy)hex-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

2: dmap / toluene / 6 h / 0 - 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; toluene; 2: Yamaguchi esterification;
DOI:10.1002/ejoc.201101603

Reference yield:

: 1379680-88-2
(3R,4R)-4-(4-methoxybenzyloxy)-5-oxopent-1-en-3-yl formate

: 1379680-83-7
(2R)-4-[(3R,4S)-4-(4-methoxybenzyloxy)pent-1-en-3-yloxy]-4-oxobutan-2-yl (4R,5S,E)-5-(acryloyloxy)-4-(tert-butyldimethylsilyloxy)hex-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 12 h / 0 - 20 °C

3: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere

4: dmap / toluene / 5 h / 0 - 20 °C / Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

6: dmap / toluene / 6 h / 0 - 20 °C / Inert atmosphere

With dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 6: Yamaguchi esterification;
DOI:10.1002/ejoc.201101603