(Z)-1-(4:6-p-methoxybenzylidene-2:3-carbonylmethylene-β-D-galactopyranosyl)-4-(tri-O-acetyl-α-L-fucopyranosyl)-2-butene

Base Information

Chemical Name:(Z)-1-(4:6-p-methoxybenzylidene-2:3-carbonylmethylene-β-D-galactopyranosyl)-4-(tri-O-acetyl-α-L-fucopyranosyl)-2-butene
CAS No.:163732-19-2
Molecular Formula:C₃₂H₄₀O₁₄
Molecular Weight:648.661
Hs Code.:

Synonyms:(Z)-1-(4:6-p-methoxybenzylidene-2:3-carbonylmethylene-β-D-galactopyranosyl)-4-(tri-O-acetyl-α-L-fucopyranosyl)-2-butene

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Chemical Property of (Z)-1-(4:6-p-methoxybenzylidene-2:3-carbonylmethylene-β-D-galactopyranosyl)-4-(tri-O-acetyl-α-L-fucopyranosyl)-2-butene

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Technology Process of (Z)-1-(4:6-p-methoxybenzylidene-2:3-carbonylmethylene-β-D-galactopyranosyl)-4-(tri-O-acetyl-α-L-fucopyranosyl)-2-butene

There total 11 articles about (Z)-1-(4:6-p-methoxybenzylidene-2:3-carbonylmethylene-β-D-galactopyranosyl)-4-(tri-O-acetyl-α-L-fucopyranosyl)-2-butene 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:

: 3068-32-4
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

: 163732-19-2
(Z)-1-(4:6-p-methoxybenzylidene-2:3-carbonylmethylene-β-D-galactopyranosyl)-4-(tri-O-acetyl-α-L-fucopyranosyl)-2-butene

Guidance literature:: Multi-step reaction with 6 steps

1: 2.) Ac₂O, pyridine, DMAP / 1.) THF, from -78 deg C to 23 deg C, 0.5 h, 2.) overnight

2: 91 percent / Amberlite IR 400 (OH-) resin, MeOH / 23 °C

3: 65 percent / toluene-p-sulphonic acid monohydrate / dimethylformamide / 50 °C

4: 1.) Bu₂SnO, 2.) Bu₄NI / 1.) toluene, reflux, 16 h, 2.) toluene, reflux, 3 h

5: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to 23 deg C

6: 1.) NaHMDS / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 30 min

With pyridine; methanol; dmap; Amberlite IR 400 (OH-) resin; sodium hexamethyldisilazane; acetic anhydride; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ozone; triphenylphosphine; In N,N-dimethyl-formamide;
DOI:10.1016/0968-0896(96)00127-7

Reference yield:

: 7404-35-5,17081-04-8,20853-37-6,27821-10-9,27821-11-0,30021-94-4,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,24332-95-4
1,2,3,4-tetra-O-acetyl-L-fucopyranose

: 163732-19-2
(Z)-1-(4:6-p-methoxybenzylidene-2:3-carbonylmethylene-β-D-galactopyranosyl)-4-(tri-O-acetyl-α-L-fucopyranosyl)-2-butene

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / BF₃*OEt₂ / acetonitrile / 20 °C

2: 1.) O₃, 2.) DMS / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT

3: NaBH₄ / methanol / 0 °C

4: 1.) CBr₄ / 1.) CH₂Cl₂, 2.) DMF, 110 deg C

5: 1.) NaHMDS / 1.) THF, -78 deg C

With sodium tetrahydroborate; 2,3-dimercapto-succinic acid; carbon tetrabromide; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; ozone; In methanol; acetonitrile;
DOI:10.1021/ja00124a037

Reference yield:

: 211304-12-0
Acetic acid (3R,4R,5R,6S)-3,5-diacetoxy-2-allyl-6-methyl-tetrahydro-pyran-4-yl ester

: 163732-19-2
(Z)-1-(4:6-p-methoxybenzylidene-2:3-carbonylmethylene-β-D-galactopyranosyl)-4-(tri-O-acetyl-α-L-fucopyranosyl)-2-butene

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) O₃, 2.) DMS / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT

2: NaBH₄ / methanol / 0 °C

3: 1.) CBr₄ / 1.) CH₂Cl₂, 2.) DMF, 110 deg C

4: 1.) NaHMDS / 1.) THF, -78 deg C

With sodium tetrahydroborate; 2,3-dimercapto-succinic acid; carbon tetrabromide; sodium hexamethyldisilazane; ozone; In methanol;
DOI:10.1021/ja00124a037