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

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-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate
• CAS No.: 444118-91-6
• Molecular Formula: C₅₃H₆₀Cl₃N₇O₂₀
• Molecular Weight: 1221.45
• Mol file: 444118-91-6.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-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl 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-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl 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-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate

There total 34 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-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl 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-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate (444118-91-6)

Guidance literature:

Multi-step reaction with 17 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

15: 63 percent / TMSOTf / CH₂Cl₂ / 4 h / -25 °C

16: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

17: 82 mg / DBU / tetrahydrofuran / 4 h / 0 - 20 °C

With pyridine; 1H-imidazole; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; trimethylsilyl trifluoromethanesulfonate; 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-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate (444118-91-6)

Guidance literature:

Multi-step reaction with 19 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

17.1: 63 percent / TMSOTf / CH₂Cl₂ / 4 h / -25 °C

18.1: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

19.1: 82 mg / DBU / tetrahydrofuran / 4 h / 0 - 20 °C

With pyridine; 1H-imidazole; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; trimethylsilyl trifluoromethanesulfonate; 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-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate (444118-91-6)

Guidance literature:

Multi-step reaction with 18 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

16: 63 percent / TMSOTf / CH₂Cl₂ / 4 h / -25 °C

17: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

18: 82 mg / DBU / tetrahydrofuran / 4 h / 0 - 20 °C

With pyridine; 1H-imidazole; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; trimethylsilyl trifluoromethanesulfonate; 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

Refernces