2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

Base Information

• Chemical Name: 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate
• CAS No.: 525593-64-0
• Molecular Formula: C₄₂H₄₉N₃O₁₃
• Molecular Weight: 803.863
• Mol file: 525593-64-0.mol

Synonyms:2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

Chemical Property of 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

There total 21 articles about 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-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: 89.0%

methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate (444118-41-6) + 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate (525593-63-9) → 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate (525593-64-0)

Guidance literature:

With 4 A molecular sieve; t-butyldimethylsiyl triflate; In dichloromethane; at -25 - 20 ℃;

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) → 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate (525593-64-0)

Guidance literature:

Multi-step reaction with 9 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: 89 percent / molecular sieves 4 Angstroem; TBSOTf / CH₂Cl₂ / -25 - 20 °C

With pyridine; dmap; sodium hydroxide; sodium hypochlorite; 4 A molecular sieve; t-butyldimethylsiyl triflate; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; (+)-10-camphorsulfonic acid; trifluoroacetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200390009

Reference yield:

benzyl bromide (100-39-0) → 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate (525593-64-0)

Guidance literature:

Multi-step reaction with 11 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: 89 percent / molecular sieves 4 Angstroem; TBSOTf / CH₂Cl₂ / -25 - 20 °C

With pyridine; dmap; sodium hydroxide; sodium hypochlorite; 4 A molecular sieve; t-butyldimethylsiyl triflate; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; (+)-10-camphorsulfonic acid; trifluoroacetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200390009

upstream raw materials:

methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate

2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate

benzaldehyde dimethyl acetal

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

Downstream raw materials:

2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

Refernces