(3S,4R)-1-N-{(2E)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)but-2-enyl}sulfonyl-3-[(1'R)-phenylethylamino]-4-benzyloxycarbonylpyrrolidine

Base Information

Chemical Name:(3S,4R)-1-N-{(2E)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)but-2-enyl}sulfonyl-3-[(1'R)-phenylethylamino]-4-benzyloxycarbonylpyrrolidine
CAS No.:911286-99-2
Molecular Formula:C₃₈H₄₈N₂O₁₄S
Molecular Weight:788.87
Hs Code.:

Synonyms:(3S,4R)-1-N-{(2E)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)but-2-enyl}sulfonyl-3-[(1'R)-phenylethylamino]-4-benzyloxycarbonylpyrrolidine

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Chemical Property of (3S,4R)-1-N-{(2E)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)but-2-enyl}sulfonyl-3-[(1'R)-phenylethylamino]-4-benzyloxycarbonylpyrrolidine

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Technology Process of (3S,4R)-1-N-{(2E)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)but-2-enyl}sulfonyl-3-[(1'R)-phenylethylamino]-4-benzyloxycarbonylpyrrolidine

There total 5 articles about (3S,4R)-1-N-{(2E)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)but-2-enyl}sulfonyl-3-[(1'R)-phenylethylamino]-4-benzyloxycarbonylpyrrolidine 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: 60.0%

: 911286-94-7
1-O-(E/Z-but-2-ene)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

: 911286-93-6
(3R,4S)-benzyl-1-(but-2-enylsulfonyl)-4-((R)-1-phenylethylamino)pyrrolidine-3-carboxylate

: 911286-99-2
(3S,4R)-1-N-{(2E)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)but-2-enyl}sulfonyl-3-[(1'R)-phenylethylamino]-4-benzyloxycarbonylpyrrolidine

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 24h;
DOI:10.1021/ja0614565

Reference yield:

: 911286-89-0
(3R,4S)-benzyl 1-tert-butyl 4-((R)-1-phenylethylamino)pyrrolidine-1,3-dicarboxylate

: 911286-99-2
(3S,4R)-1-N-{(2E)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)but-2-enyl}sulfonyl-3-[(1'R)-phenylethylamino]-4-benzyloxycarbonylpyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: TFA / CH₂Cl₂ / 1.5 h / 0 °C

1.2: 79 percent / N,N-di-iso-propylethylamine / CH₂Cl₂

2.1: 60 percent / Grubbs 2nd generation catalyst / CH₂Cl₂ / 24 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/ja0614565

Reference yield:

: 146256-98-6
4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

: 911286-99-2
(3S,4R)-1-N-{(2E)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyloxy)but-2-enyl}sulfonyl-3-[(1'R)-phenylethylamino]-4-benzyloxycarbonylpyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: AcOH / ethanol / 4 h / 20 °C

1.2: NaCNBH₃ / ethanol / 16 h / 75 °C

1.3: 25 percent / HCl / ethyl acetate; dioxane / 3 h / 0 °C

2.1: LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 2 h / 0 °C

2.2: HCl / tetrahydrofuran; methanol; H₂O / pH 5

2.3: 86 percent / Cs₂CO₃ / dimethylformamide / 3 h / 20 °C

3.1: TFA / CH₂Cl₂ / 1.5 h / 0 °C

3.2: 79 percent / N,N-di-iso-propylethylamine / CH₂Cl₂

4.1: 60 percent / Grubbs 2nd generation catalyst / CH₂Cl₂ / 24 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium hydroxide; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;
DOI:10.1021/ja0614565