(E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(4-fluorophenyl)but-3-en-2-one

Base Information

• Chemical Name: (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(4-fluorophenyl)but-3-en-2-one
• CAS No.: 1334710-59-6
• Molecular Formula: C₂₀H₂₅FO₆
• Molecular Weight: 380.413
• Mol file: 1334710-59-6.mol

Synonyms:(E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(4-fluorophenyl)but-3-en-2-one

Chemical Property of (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(4-fluorophenyl)but-3-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(4-fluorophenyl)but-3-en-2-one

There total 2 articles about (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(4-fluorophenyl)but-3-en-2-one 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: 93.0%

1-C-(4,6-O-butylidene-β-D-glucopyranosyl)propane-2-one (1253890-83-3) + 4-fluorobenzaldehyde (459-57-4) → (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(4-fluorophenyl)but-3-en-2-one (1334710-59-6)

Guidance literature:

With pyrrolidine; In dichloromethane; at 20 ℃;

DOI:10.1055/s-0030-1260111

Reference yield:

4,6-O-(1-butylidene)-D-glucopyranose (27994-33-8) → (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(4-fluorophenyl)but-3-en-2-one (1334710-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / tetrahydrofuran; water / 36 h / Reflux

2: pyrrolidine / dichloromethane / 20 °C

With pyrrolidine; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c4ra06544a

Reference yield: 83.0%

sarcosine (107-97-1,25951-24-0) + (E)-1-(4,6-O-butylidene-β-D-glucopyranosyl)-4-(4-fluorophenyl)but-3-en-2-one (1334710-59-6) + indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 3'-[2-(4,6-O-butylidene-β-D-glucopyranosyl)-1-oxoethyl]-4'-(4-fluorophenyl)-1'-methylspiro[indole-3,2'-pyrrolidin]-2(1H)-one (1334710-65-4)

Guidance literature:

In toluene; acetonitrile; for 7h; optical yield given as %de; regioselective reaction; Reflux; Inert atmosphere;

DOI:10.1055/s-0030-1260111

upstream raw materials:

1-C-(4,6-O-butylidene-β-D-glucopyranosyl)propane-2-one

4-fluorobenzaldehyde

4,6-O-(1-butylidene)-D-glucopyranose

Downstream raw materials:

3'-[2-(4,6-O-butylidene-β-D-glucopyranosyl)-1-oxoethyl]-4'-(4-fluorophenyl)-1'-methylspiro[indole-3,2'-pyrrolidin]-2(1H)-one

2'-[2-(4,6-O-butylidene-β-D-glucopyranosyl)-1-oxoethyl]-1'-(4-fluorophenyl)-1',2',5',6',7',7a'-hexahydrospiro[indole-3,3'-pyrrolizidin]-2(1H)-one

5-(4-fluorophenyl)-7-(4,6-O-butylidene-β-D-glucopyranosyl-1-methyl)-1,3-dimethylpyrido[2,3-d]pyrimidine-2,4(1H,3H)dione