benzyl (2S,3R,5R)-5-allyl-2,3-dimethoxy-5-(2-methoxycarbonylallyl)-2,3-dimethyl-6-oxomorpholine-4-carboxylate

Base Information

Chemical Name:benzyl (2S,3R,5R)-5-allyl-2,3-dimethoxy-5-(2-methoxycarbonylallyl)-2,3-dimethyl-6-oxomorpholine-4-carboxylate
CAS No.:763101-66-2
Molecular Formula:C₂₄H₃₁NO₈
Molecular Weight:461.512
Hs Code.:

Synonyms:benzyl (2S,3R,5R)-5-allyl-2,3-dimethoxy-5-(2-methoxycarbonylallyl)-2,3-dimethyl-6-oxomorpholine-4-carboxylate

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Chemical Property of benzyl (2S,3R,5R)-5-allyl-2,3-dimethoxy-5-(2-methoxycarbonylallyl)-2,3-dimethyl-6-oxomorpholine-4-carboxylate

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Technology Process of benzyl (2S,3R,5R)-5-allyl-2,3-dimethoxy-5-(2-methoxycarbonylallyl)-2,3-dimethyl-6-oxomorpholine-4-carboxylate

There total 3 articles about benzyl (2S,3R,5R)-5-allyl-2,3-dimethoxy-5-(2-methoxycarbonylallyl)-2,3-dimethyl-6-oxomorpholine-4-carboxylate 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: 79.0%

: 4224-69-5
methyl 2-(bromomethyl)propenoate

: 565234-18-6
benzyl (2S,3R,5R)-5-allyl-2,3-dimethoxy-2,3-dimethyl-6-oxomorpholine-4-carboxylate

: 763101-66-2
benzyl (2S,3R,5R)-5-allyl-2,3-dimethoxy-5-(2-methoxycarbonylallyl)-2,3-dimethyl-6-oxomorpholine-4-carboxylate

Guidance literature:: With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -55 ℃; for 21h;
DOI:10.1016/j.tet.2004.06.063

Reference yield:

: 565234-16-4
(2S,3R)-2,3-Dimethoxy-2,3-dimethyl-6-methylene-morpholine-4-carboxylic acid benzyl ester

: 763101-66-2
benzyl (2S,3R,5R)-5-allyl-2,3-dimethoxy-5-(2-methoxycarbonylallyl)-2,3-dimethyl-6-oxomorpholine-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / aq. NaIO₄; RuCl₃; NaHCO₃ / acetonitrile; CCl₄ / 2 h / 20 °C

2: 73 percent / BuLi; diisopropylamine; HMPA / tetrahydrofuran; hexane / 21 h / -55 °C

3: 79 percent / lithium diisopropylamide; TMEDA / tetrahydrofuran; hexane / 21 h / -55 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; ruthenium trichloride; sodium periodate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; hexane; acetonitrile;
DOI:10.1016/j.tet.2004.06.063

Reference yield:

: 565234-15-3
benzyl (2S,3R,6S)-6-(bromomethyl)-2,3-dimethoxy-2,3-dimethylmorpholine-4-carboxylate

: 763101-66-2
benzyl (2S,3R,5R)-5-allyl-2,3-dimethoxy-5-(2-methoxycarbonylallyl)-2,3-dimethyl-6-oxomorpholine-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 64 percent / KHMDS / tetrahydrofuran; toluene / -78 - 20 °C

2: 85 percent / aq. NaIO₄; RuCl₃; NaHCO₃ / acetonitrile; CCl₄ / 2 h / 20 °C

3: 73 percent / BuLi; diisopropylamine; HMPA / tetrahydrofuran; hexane / 21 h / -55 °C

4: 79 percent / lithium diisopropylamide; TMEDA / tetrahydrofuran; hexane / 21 h / -55 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; ruthenium trichloride; sodium periodate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium hexamethylsilazane; sodium hydrogencarbonate; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; hexane; toluene; acetonitrile;
DOI:10.1016/j.tet.2004.06.063