(E)-2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxymethylene)cyclohexanone

Base Information

• Chemical Name: (E)-2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxymethylene)cyclohexanone
• CAS No.: 184824-72-4
• Molecular Formula: C₂₁H₂₈O₁₁
• Molecular Weight: 456.447
• Mol file: 184824-72-4.mol

Synonyms:(E)-2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxymethylene)cyclohexanone

Chemical Property of (E)-2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxymethylene)cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxymethylene)cyclohexanone

There total 2 articles about (E)-2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxymethylene)cyclohexanone 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: 27.0%

2-hydroxymethylene cyclohexanone sodium salt + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (E)-2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxymethylene)cyclohexanone (184824-72-4)

Guidance literature:

In water; acetone; for 24h;

DOI:10.1039/P19960002487

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (E)-2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxymethylene)cyclohexanone (184824-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / diethyl ether / 15 h / Ambient temperature

2: 27 percent / acetone; H₂O / 24 h

With sodium methylate; In diethyl ether; water; acetone;

DOI:10.1039/P19960002487

Reference yield: 20.0%

propan-1-ol (71-23-8) + (E)-2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxymethylene)cyclohexanone (184824-72-4) → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (3947-62-4) + 2,3,4,6-tetraacetylglucose (3947-62-4,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,6207-76-7) + (2R)-2-bromo-2-[(R)-propoxy-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)methyl]cyclohexanone + (2S)-2-bromo-2-[(S)-propoxy-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)methyl]cyclohexanone

Guidance literature:

With N-Bromosuccinimide; for 2h;

DOI:10.1039/b002749i

upstream raw materials:

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

cyclohexanone

Downstream raw materials:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

2,3,4,6-tetraacetylglucose