(3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]tetrahydrofuran-2-one

Base Information

Chemical Name:(3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]tetrahydrofuran-2-one
CAS No.:186694-68-8
Molecular Formula:C₂₆H₃₅NO₆Si
Molecular Weight:485.653
Hs Code.:

Synonyms:(3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]tetrahydrofuran-2-one

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Chemical Property of (3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]tetrahydrofuran-2-one

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Technology Process of (3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]tetrahydrofuran-2-one

There total 7 articles about (3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]tetrahydrofuran-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: 95.0%

: 3634-56-8
isopropyldimethylsilyl chloride

: 186694-63-3
(3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-(1-hydroxyethyl)tetrahydrofuran-2-one

: 186694-68-8
(3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]tetrahydrofuran-2-one

Guidance literature:: With 1H-imidazole; In tetrahydrofuran; for 1h; Ambient temperature;
DOI:10.1055/s-1997-696

Reference yield:

: 182216-93-9
(R)-((2R,5S)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methanol

: 186694-68-8
(3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 0.5 h / 0 °C

1.2: 85 percent / Bu₄NI / tetrahydrofuran / 12 h / 20 °C

2.1: 88 percent / 0.25N HCl / 5 h / 20 °C

3.1: 98 percent / Na₂CO₃; NaHCO₃ / dioxane; H₂O / 1 h / 20 °C

4.1: 85 percent / TFA / tetrahydrofuran; H₂O / 3 h / 20 °C

5.1: 95 percent / imidazole / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium hydrogencarbonate; sodium carbonate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; water;
DOI:10.1016/S0957-4166(02)00376-2

Reference yield:

: 186694-55-3
ethyl (2R,3R,4S,5R)-2-amino-3-benzyloxy-4,5-isopropylidenedioxyhexanoate

: 186694-68-8
(3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / Na₂CO₃; NaHCO₃ / dioxane; H₂O / 1 h / 20 °C

2: 85 percent / TFA / tetrahydrofuran; H₂O / 3 h / 20 °C

3: 95 percent / imidazole / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; sodium hydrogencarbonate; sodium carbonate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; water;
DOI:10.1016/S0957-4166(02)00376-2