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

Base Information

• Chemical Name: 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-α-D-glucopyranosyluronate trichloroacetimidate
• CAS No.: 444118-69-8
• Molecular Formula: C₄₃H₄₇Cl₃N₄O₁₄
• Molecular Weight: 950.224
• Mol file: 444118-69-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 27 articles about 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-α-D-glucopyranosyluronate trichloroacetimidate 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:

(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) → 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-α-D-glucopyranosyluronate trichloroacetimidate (444118-69-8)

Guidance literature:

Multi-step reaction with 14 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: 83 percent / molecular sieves 4 Angstroem; TBSOTf / CH₂Cl₂ / -78 - 20 °C

10: 84 percent / aq. dichloroacetic acid / 2 h / 20 °C

11: 80 percent / imidazole / CH₂Cl₂ / 40 h

12: 100 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

13: glacial AcOH; TBAF / tetrahydrofuran / 0.67 h

14: 302 mg / DBU / CH₂Cl₂ / 2 h

With pyridine; 1H-imidazole; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; 4 A molecular sieve; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-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) → 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-α-D-glucopyranosyluronate trichloroacetimidate (444118-69-8)

Guidance literature:

Multi-step reaction with 16 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: 83 percent / molecular sieves 4 Angstroem; TBSOTf / CH₂Cl₂ / -78 - 20 °C

12.1: 84 percent / aq. dichloroacetic acid / 2 h / 20 °C

13.1: 80 percent / imidazole / CH₂Cl₂ / 40 h

14.1: 100 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

15.1: glacial AcOH; TBAF / tetrahydrofuran / 0.67 h

16.1: 302 mg / DBU / CH₂Cl₂ / 2 h

With pyridine; 1H-imidazole; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; 4 A molecular sieve; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-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:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-α-D-glucopyranosyluronate trichloroacetimidate (444118-69-8)

Guidance literature:

Multi-step reaction with 15 steps

1: aq. AcOH / 20 h / 20 - 40 °C

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

3: pyridine; DMAP / 20 °C

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

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

6: aq. NaOH / methanol / 20 °C

7: 44 g / KHCO₃ / dimethylformamide / 20 °C

8: 100 percent / aq. TFA / 0.25 h / 20 °C

9: 48 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 0 - 20 °C

10: 83 percent / molecular sieves 4 Angstroem; TBSOTf / CH₂Cl₂ / -78 - 20 °C

11: 84 percent / aq. dichloroacetic acid / 2 h / 20 °C

12: 80 percent / imidazole / CH₂Cl₂ / 40 h

13: 100 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

14: glacial AcOH; TBAF / tetrahydrofuran / 0.67 h

15: 302 mg / DBU / CH₂Cl₂ / 2 h

With pyridine; 1H-imidazole; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; 4 A molecular sieve; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-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:

trichloroacetonitrile

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

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid

benzyl bromide

Downstream raw materials:

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate

tert-butyldimethylsilyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside