6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-monochloroacetyl-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-monochloroacetyl-α-D-glucopyranosyluronate trichloroacetimidate
CAS No.:444118-61-0
Molecular Formula:C₄₀H₄₂Cl₄N₄O₁₃
Molecular Weight:928.604
Hs Code.:

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

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

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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-monochloroacetyl-α-D-glucopyranosyluronate trichloroacetimidate

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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-monochloroacetyl-α-D-glucopyranosyluronate trichloroacetimidate

There total 26 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-monochloroacetyl-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: 90.0%

: 545-06-2
trichloroacetonitrile

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

: 444118-61-0
6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-monochloroacetyl-α-D-glucopyranosyluronate trichloroacetimidate

Guidance literature:: With 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃; for 1h;
DOI:10.1002/chem.200390009

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 444118-61-0
6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-monochloroacetyl-α-D-glucopyranosyluronate trichloroacetimidate

Guidance literature:: Multi-step reaction with 13 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: 93 percent / pyridine; DMAP / CH₂Cl₂ / 6 h / 20 °C

12: 76 percent / BnNH₂ / diethyl ether / -20 °C

13: 90 percent / molecular sieves 4 Angstroem; DBU / CH₂Cl₂ / 1 h / 0 - 20 °C

With pyridine; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; 4 A molecular sieve; t-butyldimethylsiyl triflate; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; benzylamine; trifluoroacetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200390009

Reference yield:

: 18685-18-2
3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

: 444118-61-0
6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-monochloroacetyl-α-D-glucopyranosyluronate trichloroacetimidate

Guidance literature:: Multi-step reaction with 14 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: 93 percent / pyridine; DMAP / CH₂Cl₂ / 6 h / 20 °C

13: 76 percent / BnNH₂ / diethyl ether / -20 °C

14: 90 percent / molecular sieves 4 Angstroem; DBU / CH₂Cl₂ / 1 h / 0 - 20 °C

With pyridine; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; 4 A molecular sieve; t-butyldimethylsiyl triflate; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; benzylamine; trifluoroacetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200390009