Benzyl (2E,4E)-5-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranoyloxy)penta-2,4-dienoate

Base Information

• Chemical Name: Benzyl (2E,4E)-5-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranoyloxy)penta-2,4-dienoate
• CAS No.: 152094-22-9
• Molecular Formula: C₂₆H₃₀O₁₂
• Molecular Weight: 534.517

Synonyms:Benzyl (2E,4E)-5-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranoyloxy)penta-2,4-dienoate

Chemical Property of Benzyl (2E,4E)-5-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranoyloxy)penta-2,4-dienoate

Chemical Property:

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Technology Process of Benzyl (2E,4E)-5-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranoyloxy)penta-2,4-dienoate

There total 5 articles about Benzyl (2E,4E)-5-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranoyloxy)penta-2,4-dienoate 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: 62.0%

(2E)-3-(2`,3`,4`,6`-tetra-O-acetyl-Β-D-glucopyranosyloxy)propenal (106758-59-2) + (Tributyl-λ5-phosphanylidene)-acetic acid benzyl ester (152094-21-8) → Benzyl (2E,4E)-5-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranoyloxy)penta-2,4-dienoate (152094-22-9) + (3Z,5E)-6-((2R,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexa-3,5-dienoic acid benzyl ester

Guidance literature:

In dichloromethane; for 18h;

Reference yield: 56.0%

(2E)-3-(2`,3`,4`,6`-tetra-O-acetyl-Β-D-glucopyranosyloxy)propenal (106758-59-2) + (Tributyl-λ5-phosphanylidene)-acetic acid benzyl ester (152094-21-8) → Benzyl (2E,4E)-5-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranoyloxy)penta-2,4-dienoate (152094-22-9)

Guidance literature:

DOI:10.1039/c39930001179

Reference yield: 48.0%

(carbobenzyloxymethylene)triphenylphosphorane (15097-38-8) + (2E)-3-(2`,3`,4`,6`-tetra-O-acetyl-Β-D-glucopyranosyloxy)propenal (106758-59-2) → Benzyl (2E,4E)-5-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranoyloxy)penta-2,4-dienoate (152094-22-9)

Guidance literature:

In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(02)02534-0

upstream raw materials:

(2E)-3-(2`,3`,4`,6`-tetra-O-acetyl-Β-D-glucopyranosyloxy)propenal

(Tributyl-λ⁵-phosphanylidene)-acetic acid benzyl ester

(carbobenzyloxymethylene)triphenylphosphorane

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

Benzyl (3S,6S)-1,2-bis(tert-butoxycarbonyl)-1,2,3,6-tetrahydro-6-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranosyloxy)pyridazine-3-carboxylate

Methyl (3S,6S)-1,2-bis(benzyloxycarbonyl)-1,2,3,6-tetrahydro-6-(2`,3`,4`,6`-tetra-O-acetyl-β-D-glucopyranosyloxy)pyridazine-3-carboxylate

(5S,8S)-2-(2-Benzenesulfonyl-ethyl)-1,3-dioxo-8-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2,3,5,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid benzyl ester

2-(2-benzenesulfonyl-ethyl)-1,3-dioxo-hexahydro-[1,2,4]triazolo[1,2-a]pyridazine-5-carboxylic acid

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