pent-4-enyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

Base Information

Chemical Name:pent-4-enyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside
CAS No.:525593-57-1
Molecular Formula:C₂₅H₃₃N₃O₈
Molecular Weight:503.552
Hs Code.:

Synonyms:pent-4-enyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

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Chemical Property of pent-4-enyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

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Technology Process of pent-4-enyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

There total 11 articles about pent-4-enyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside 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: 75.0%

: 821-09-0
n-Pent-4-enyl alcohol

: 525593-51-5
6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate

: 525593-57-1
pent-4-enyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: With boron trifluoride diethyl etherate; In hexane; dichloromethane; for 0.5h;
DOI:10.1002/chem.200390009

Reference yield:

: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 525593-57-1
pent-4-enyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 29.8 g / imidazole / CH₂Cl₂ / 2 h

2: NaOMe; MeOH / 0.25 h

3: 29.0 g / p-TsOH*H₂O / acetonitrile / 20 °C

4: 95 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 8 h

5: 92 percent / aq. TFA / CH₂Cl₂ / 8.5 h / 20 °C

6: 96 percent / 2,4,6-collidine / -40 °C

7: 96 percent / DMAP / CH₂Cl₂ / 5 h / 20 °C

8: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

9: DBU / CH₂Cl₂ / 1 h / 0 °C

10: 75 percent / BF₃*Et₂O / CH₂Cl₂; hexane / 0.5 h

With 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; dmap; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;
DOI:10.1002/chem.200390009

Reference yield:

: 99049-67-9
tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid

: 525593-57-1
pent-4-enyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 29.0 g / p-TsOH*H₂O / acetonitrile / 20 °C

2: 95 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 8 h

3: 92 percent / aq. TFA / CH₂Cl₂ / 8.5 h / 20 °C

4: 96 percent / 2,4,6-collidine / -40 °C

5: 96 percent / DMAP / CH₂Cl₂ / 5 h / 20 °C

6: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

7: DBU / CH₂Cl₂ / 1 h / 0 °C

8: 75 percent / BF₃*Et₂O / CH₂Cl₂; hexane / 0.5 h

With 2,4,6-trimethyl-pyridine; dmap; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;
DOI:10.1002/chem.200390009