(EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene

Base Information

• Chemical Name: (EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene
• CAS No.: 1432614-63-5
• Molecular Formula: C₂₄H₂₇ClO₉
• Molecular Weight: 494.926

Synonyms:(EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene

Chemical Property of (EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene

Chemical Property:

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Technology Process of (EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene

There total 2 articles about (EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene 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%

(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2(R/S)-hydroxy-4-(4-chlorophenyl)but-3-ene → (EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene (1432614-63-5) + (ZE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene (1432615-04-7)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 40 ℃; for 4.25h; Overall yield = 84 %; stereoselective reaction; Green chemistry;

DOI:10.1021/jo302589t

Reference yield:

(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-3-en-2-one (1042966-22-2) → (EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene (1432614-63-5) + (ZE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene (1432615-04-7)

Guidance literature:

Multi-step reaction with 2 steps

1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.5 h / 0 °C

2: triethylamine; methanesulfonyl chloride / dichloromethane / 4.25 h / 0 - 40 °C / Green chemistry

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; methanesulfonyl chloride; triethylamine; In methanol; dichloromethane; 1: |Luche Cerium Reduction;

DOI:10.1021/jo302589t

Reference yield:

(EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-1,3-diene (1432614-63-5) + [1,4]naphthoquinone (130-15-4) → 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)anthracene-9,10-(1H,4H)dione

Guidance literature:

With indium(III) chloride tetrahydrate; In toluene; at 80 ℃; for 3h; Green chemistry;

DOI:10.1021/jo302589t

upstream raw materials:

(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)but-3-en-2-one

Downstream raw materials:

1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-chlorophenyl)anthracene-9,10-dione

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