(ZE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-1,3-diene

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Chemical Name:(ZE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-1,3-diene
CAS No.:1432615-86-5
Molecular Formula:C₂₄H₂₈O₉
Molecular Weight:460.481
Hs Code.:

Synonyms:(ZE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-1,3-diene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 2 articles about (ZE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-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: 70.0%

: (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2(R/S)-hydroxy-4-phenyl but-3-ene

: 1432614-61-3
(EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-1,3-diene

: 1432615-86-5
(ZE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-1,3-diene

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 40 ℃; for 4.25h; Overall yield = 91 %; stereoselective reaction; Green chemistry;
DOI:10.1021/jo302589t

Reference yield:

: 1042966-18-6
(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-3-en-2-one

: 1432614-61-3
(EE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-1,3-diene

: 1432615-86-5
(ZE)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-phenylbut-1,3-diene

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