(1E,3E,5E)-6-bromo-1-{4-benzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone}-1,3,5-hexatriene

Base Information

Chemical Name:(1E,3E,5E)-6-bromo-1-{4-benzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone}-1,3,5-hexatriene
CAS No.:942499-69-6
Molecular Formula:C₅₂H₄₉BrO₈
Molecular Weight:881.86
Hs Code.:

Synonyms:(1E,3E,5E)-6-bromo-1-{4-benzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone}-1,3,5-hexatriene

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Chemical Property of (1E,3E,5E)-6-bromo-1-{4-benzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone}-1,3,5-hexatriene

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Technology Process of (1E,3E,5E)-6-bromo-1-{4-benzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone}-1,3,5-hexatriene

There total 5 articles about (1E,3E,5E)-6-bromo-1-{4-benzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone}-1,3,5-hexatriene 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%

: 942499-62-9
4-benzyloxy-6-methyl-3-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone

: 168295-33-8
(2E,4E)-5-bromopenta-2,4-dienal

: 942499-69-6
(1E,3E,5E)-6-bromo-1-{4-benzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone}-1,3,5-hexatriene

: 942499-68-5
C₅₂H₅₁BrO₉

Guidance literature:: 4-benzyloxy-6-methyl-3-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

(2E,4E)-5-bromopenta-2,4-dienal; With scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; at -78 ℃; for 2.5h; Further stages.;
DOI:10.1248/cpb.55.495

Reference yield:

: 100-51-6,185532-71-2
benzyl alcohol

: 942499-69-6
(1E,3E,5E)-6-bromo-1-{4-benzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone}-1,3,5-hexatriene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 86 percent / PPh₃; DIAD / tetrahydrofuran; toluene / 2 h / 20 °C

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 1 percent / Sc(OTf)3 / tetrahydrofuran / 2.5 h / -78 °C

With di-isopropyl azodicarboxylate; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1248/cpb.55.495

Reference yield:

: 590410-81-4
C³-β-D-galactopyranosyl-4-hydroxy-2-pyrone

: 942499-69-6
(1E,3E,5E)-6-bromo-1-{4-benzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone}-1,3,5-hexatriene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 86 percent / PPh₃; DIAD / tetrahydrofuran; toluene / 2 h / 20 °C

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 1 percent / Sc(OTf)3 / tetrahydrofuran / 2.5 h / -78 °C

With di-isopropyl azodicarboxylate; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;
DOI:10.1248/cpb.55.495