(E)-3-[4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]prop-2-en-1-ol

Base Information

Chemical Name:(E)-3-[4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]prop-2-en-1-ol
CAS No.:134660-05-2
Molecular Formula:C₂₃H₂₈O₁₁
Molecular Weight:480.469
Hs Code.:

Synonyms:(E)-3-[4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]prop-2-en-1-ol

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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 (E)-3-[4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]prop-2-en-1-ol

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Technology Process of (E)-3-[4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]prop-2-en-1-ol

There total 6 articles about (E)-3-[4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]prop-2-en-1-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: 92.0%

: 203179-61-7
4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde

: 134660-05-2
(E)-3-[4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]prop-2-en-1-ol

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 20 ℃; for 1.5h;
DOI:10.1055/s-1998-2009

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-glucose pentaacetate

: 134660-05-2
(E)-3-[4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 35percent HBr / acetic acid

2: 24 percent / TDA-1, aq. K₂CO₃ / CH₂Cl₂ / 72 h / 39 °C

3: 43.5 percent / TDA-1, aq. K₂CO₃ / CH₂Cl₂ / 15 h / Heating

4: 1.) Br₂, 2.) aq. AcOH / 1.) CCl₄, 20 deg C, 1 h, 2.) r.t., 10 h

5: 92 percent / NaBH₄ / tetrahydrofuran; methanol / 1.5 h / 20 °C

With sodium tetrahydroborate; hydrogen bromide; bromine; potassium carbonate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; acetic acid;
DOI:10.1055/s-1998-2009

Reference yield:

: 123-08-0,65581-83-1
4-hydroxy-benzaldehyde

: 134660-05-2
(E)-3-[4-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 24 percent / TDA-1, aq. K₂CO₃ / CH₂Cl₂ / 72 h / 39 °C

2: 43.5 percent / TDA-1, aq. K₂CO₃ / CH₂Cl₂ / 15 h / Heating

3: 1.) Br₂, 2.) aq. AcOH / 1.) CCl₄, 20 deg C, 1 h, 2.) r.t., 10 h

4: 92 percent / NaBH₄ / tetrahydrofuran; methanol / 1.5 h / 20 °C

With sodium tetrahydroborate; bromine; potassium carbonate; acetic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1055/s-1998-2009