(4S)-4-benzyl-3-{(2R,3S,6S,E)-3-[(tert-butyldimethylsilyl)oxy]-2,4,6,8-tetra-methylnona-4,7-dienoyl}oxazolidin-2-one

Base Information

Chemical Name:(4S)-4-benzyl-3-{(2R,3S,6S,E)-3-[(tert-butyldimethylsilyl)oxy]-2,4,6,8-tetra-methylnona-4,7-dienoyl}oxazolidin-2-one
CAS No.:1268687-80-4
Molecular Formula:C₂₉H₄₅NO₄Si
Molecular Weight:499.766
Hs Code.:

Synonyms:(4S)-4-benzyl-3-{(2R,3S,6S,E)-3-[(tert-butyldimethylsilyl)oxy]-2,4,6,8-tetra-methylnona-4,7-dienoyl}oxazolidin-2-one

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Chemical Property of (4S)-4-benzyl-3-{(2R,3S,6S,E)-3-[(tert-butyldimethylsilyl)oxy]-2,4,6,8-tetra-methylnona-4,7-dienoyl}oxazolidin-2-one

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Technology Process of (4S)-4-benzyl-3-{(2R,3S,6S,E)-3-[(tert-butyldimethylsilyl)oxy]-2,4,6,8-tetra-methylnona-4,7-dienoyl}oxazolidin-2-one

There total 1 articles about (4S)-4-benzyl-3-{(2R,3S,6S,E)-3-[(tert-butyldimethylsilyl)oxy]-2,4,6,8-tetra-methylnona-4,7-dienoyl}oxazolidin-2-one 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: 82.0%

: (4S)-4-benzyl-3-[(3S,6S,E)-3-hydroxy-2,4,6,8-tetramethylnona-4,7-dienoyl]oxazolidin-2-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 1268687-80-4
(4S)-4-benzyl-3-{(2R,3S,6S,E)-3-[(tert-butyldimethylsilyl)oxy]-2,4,6,8-tetra-methylnona-4,7-dienoyl}oxazolidin-2-one

: (4S)-4-benzyl-3-{(2S,3S,6S,E)-3-[(tert-butyldimethylsilyl)oxy]-2,4,6,8-tetra-methylnona-4,7-dienoyl}oxazolidin-2-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -10 - 20 ℃; for 4.5h; optical yield given as %de; Inert atmosphere;
DOI:10.1002/anie.201005605

Reference yield:

: 1268687-80-4
(4S)-4-benzyl-3-{(2R,3S,6S,E)-3-[(tert-butyldimethylsilyl)oxy]-2,4,6,8-tetra-methylnona-4,7-dienoyl}oxazolidin-2-one

: 1268687-88-2
(5S,6S,7S,10S,12S,13S)-13-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tri-decamethyl-4,14-dioxa-3,15-disilaheptadecan-9-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium borohydride / tetrahydrofuran; methanol; diethyl ether / 5 h / 0 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.58 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: calcium hydride; boron trifluoride diethyl etherate / dichloromethane / 3.75 h / -95 - -78 °C / Inert atmosphere

With lithium borohydride; calcium hydride; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Mukaiyama reaction;
DOI:10.1002/anie.201005605

Reference yield:

: 1268687-80-4
(4S)-4-benzyl-3-{(2R,3S,6S,E)-3-[(tert-butyldimethylsilyl)oxy]-2,4,6,8-tetra-methylnona-4,7-dienoyl}oxazolidin-2-one

: 1268688-00-1
O-{(5S,6S,7S,8S,11S,12S,13S)-5-[(S,E)-4,6-dimethylhepta-2,5-dien-2-yl]-11-methoxy-13-[2-({4-methoxybenzyl}oxy)ethyl]-2,2,3,3,6,8,10,10,12,15,15,16,16-tridecamethyl-9-oxo-4,14-dioxa-3,15-disilaheptadecan-7-yl} S-methyl dithiocarbonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium borohydride / tetrahydrofuran; methanol; diethyl ether / 5 h / 0 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.58 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: calcium hydride; boron trifluoride diethyl etherate / dichloromethane / 3.75 h / -95 - -78 °C / Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 6 h / -78 - 0 °C / Inert atmosphere

With lithium borohydride; calcium hydride; oxalyl dichloride; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; dimethyl sulfoxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Mukaiyama reaction;
DOI:10.1002/anie.201005605