4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-3-E-buten-2(S)-ol

Base Information

Chemical Name:4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-3-E-buten-2(S)-ol
CAS No.:918334-61-9
Molecular Formula:C₅₄H₇₂O₈
Molecular Weight:849.161
Hs Code.:

Synonyms:4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-3-E-buten-2(S)-ol

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Chemical Property of 4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-3-E-buten-2(S)-ol

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Technology Process of 4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-3-E-buten-2(S)-ol

There total 7 articles about 4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-3-E-buten-2(S)-ol 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: 69.0%

: 4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-3-ene-1,2-diol

: 57-10-3
1-hexadecylcarboxylic acid

: 918334-61-9
4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-3-E-buten-2(S)-ol

Guidance literature:: With dmap; dicyclohexyl-carbodiimide;
DOI:10.1016/j.carres.2009.02.032

Reference yield:

: 1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranode

: 918334-61-9
4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-3-E-buten-2(S)-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: trimethylsilyl iodide / CH₂Cl₂ / 1 h / 0 °C

2.1: tetrabutylammonium iodide / toluene / 0.08 h / 110 °C

2.2: tetrahydrofuran; toluene / 110 °C

3.1: 82 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 96 h / 45 °C

4.1: NaOMe / CH₂Cl₂; methanol / 0.67 h / 20 °C

5.1: 33 mg / DMAP / CH₂Cl₂ / 12 h / 20 °C

With dmap; trimethylsilyl iodide; sodium methylate; tetra-(n-butyl)ammonium iodide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In methanol; dichloromethane; toluene;
DOI:10.1021/ol062354m

Reference yield:

: 53008-62-1,53008-61-0
2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide

: 918334-61-9
4-C-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-O-palmitoyl-3-E-buten-2(S)-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrabutylammonium iodide / toluene / 0.08 h / 110 °C

1.2: tetrahydrofuran; toluene / 110 °C

2.1: 82 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 96 h / 45 °C

3.1: NaOMe / CH₂Cl₂; methanol / 0.67 h / 20 °C

4.1: 33 mg / DMAP / CH₂Cl₂ / 12 h / 20 °C

With dmap; sodium methylate; tetra-(n-butyl)ammonium iodide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In methanol; dichloromethane; toluene;
DOI:10.1021/ol062354m