pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

Base Information

• Chemical Name: pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate
• CAS No.: 444118-76-7
• Molecular Formula: C₃₉H₄₉N₃O₁₄
• Molecular Weight: 783.83

Synonyms:pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

Chemical Property of pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

There total 20 articles about pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 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: 85.0%

pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate (444118-75-6) → pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate (444118-76-7)

Guidance literature:

With pyridine hydrogenfluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 93h;

DOI:10.1002/chem.200390009

Reference yield:

benzyl bromide (100-39-0) → pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate (444118-76-7)

Guidance literature:

Multi-step reaction with 18 steps

1.1: NaH / tetrahydrofuran

1.2: Bu₄NI / tetrahydrofuran / 10 h / 20 °C

2.1: aq. AcOH / 20 h / 20 - 40 °C

3.1: pyridine; DMAP / CH₂Cl₂ / 19 h / 20 °C

4.1: pyridine; DMAP / 20 °C

5.1: HF*pyridine; pyridine / tetrahydrofuran / 20 °C

6.1: NaOCl; aq. NaHCO₃; KBr / TEMPO; Bu₄NBr / CH₂Cl₂ / 0.5 h

7.1: aq. NaOH / methanol / 20 °C

8.1: 44 g / KHCO₃ / dimethylformamide / 20 °C

9.1: 100 percent / aq. TFA / 0.25 h / 20 °C

10.1: 48 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 0 - 20 °C

11.1: 80 percent / molecular sieves 4 Angstroem; AgClO₄; SnCl₂ / diethyl ether / 23.5 h / 0 - 12 °C

12.1: 81 percent / aq. dichloroacetic acid / 1 h / 20 °C

13.1: 84 percent / imidazole / CH₂Cl₂ / 40 h

14.1: 97 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

15.1: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

16.1: 1.0 g / DBU / CH₂Cl₂ / 4 h / 0 - 20 °C

17.1: 75 percent / TMSOTf / toluene / 2 h / 0 - 20 °C

18.1: 85 percent / glacial AcOH; HF*pyridine / tetrahydrofuran / 93 h / 20 °C

With pyridine; 1H-imidazole; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver perchlorate; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; trifluoroacetic acid; tin(ll) chloride; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.200390009

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate (444118-76-7)

Guidance literature:

Multi-step reaction with 16 steps

1: pyridine; DMAP / CH₂Cl₂ / 19 h / 20 °C

2: pyridine; DMAP / 20 °C

3: HF*pyridine; pyridine / tetrahydrofuran / 20 °C

4: NaOCl; aq. NaHCO₃; KBr / TEMPO; Bu₄NBr / CH₂Cl₂ / 0.5 h

5: aq. NaOH / methanol / 20 °C

6: 44 g / KHCO₃ / dimethylformamide / 20 °C

7: 100 percent / aq. TFA / 0.25 h / 20 °C

8: 48 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 0 - 20 °C

9: 80 percent / molecular sieves 4 Angstroem; AgClO₄; SnCl₂ / diethyl ether / 23.5 h / 0 - 12 °C

10: 81 percent / aq. dichloroacetic acid / 1 h / 20 °C

11: 84 percent / imidazole / CH₂Cl₂ / 40 h

12: 97 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

13: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

14: 1.0 g / DBU / CH₂Cl₂ / 4 h / 0 - 20 °C

15: 75 percent / TMSOTf / toluene / 2 h / 0 - 20 °C

16: 85 percent / glacial AcOH; HF*pyridine / tetrahydrofuran / 93 h / 20 °C

With pyridine; 1H-imidazole; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver perchlorate; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; trifluoroacetic acid; tin(ll) chloride; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.200390009

upstream raw materials:

pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

Downstream raw materials:

pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

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