cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 2-propenyl ester

Base Information

Chemical Name:cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 2-propenyl ester
CAS No.:929879-89-0
Molecular Formula:C₂₁H₃₀O₁₀
Molecular Weight:442.463
Hs Code.:

Synonyms:cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 2-propenyl ester

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Chemical Property of cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 2-propenyl ester

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Technology Process of cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 2-propenyl ester

There total 5 articles about cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 2-propenyl ester 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: 32.0%

: 929879-84-5
2,3,4-tri-O-acetyl-1-(2,2,2-trichloroethanimidate)-α-D-glucopyranuronic acid 2-propenyl ester

: 108-93-0
cyclohexanol

: 929879-89-0
cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 2-propenyl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.666667h;
DOI:10.1002/chem.200601111

Reference yield:

: allyl 3,4,5-tri(acetyloxy)-6-hydroxytetrahydro-2H-2-pyrancarboxylate

: 929879-89-0
cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 2-propenyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 63 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 4 h / 20 °C

2: 32 percent / TMSOTf / CH₂Cl₂ / 0.67 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;
DOI:10.1002/chem.200601111

Reference yield:

: 474426-72-7
acetic 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic anhydride

: 929879-89-0
cyclohexyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 2-propenyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: H₂O / tetrahydrofuran

1.2: (COCl)2 / dimethylformamide

2.1: pyridine

3.1: 57 percent / benzylamine / tetrahydrofuran / 20 °C

4.1: 63 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 4 h / 20 °C

5.1: 32 percent / TMSOTf / CH₂Cl₂ / 0.67 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; benzylamine; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1002/chem.200601111