benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside

Base Information

Chemical Name:benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside
CAS No.:434948-85-3
Molecular Formula:C₂₉H₂₉NO₆
Molecular Weight:487.552
Hs Code.:

Synonyms:benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside

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Chemical Property of benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside

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Technology Process of benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside

There total 1 articles about benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside 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: 85.0%

: 102-92-1,17082-09-6
Cinnamoyl chloride

: 195006-98-5
benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside

: 434948-85-3
benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃;
DOI:10.1016/S0957-4166(01)00562-6

Reference yield:

: 434948-85-3
benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside

: 434949-13-0
benzyl (R)-4,6-O-benzylidene-2-deoxy-2-[(R)-2-hydroxy-3-phenylpropanamido]-β-D-allopyranoside

: 434949-11-8
benzyl (R)-4,6-O-benzylidene-2-deoxy-2-[(S)-2-hydroxy-3-phenylpropanamido]-β-D-allopyranoside

Guidance literature:: benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 48h;

With lithium aluminium tetrahydride; In tetrahydrofuran; at -10 ℃;
DOI:10.1016/S0957-4166(01)00562-6

Reference yield:

: 434948-85-3
benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside

: benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(3-hydroxybutanamido)-β-D-allopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / NaOH; tetrabutylammonium bromide / CH₂Cl₂; H₂O / 48 h / Heating

2.1: 85 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

3.1: sodium borohydride / tetrahydrofuran / 20 °C

4.1: 90 percent / 4-(N,N-dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 4 h / 20 °C

5.1: m-chloroperoxybenzoic acid / CH₂Cl₂ / 20 °C

5.2: 86 percent / LiAlH₄ / tetrahydrofuran / -10 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/S0957-4166(01)00562-6