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

Base Information

Chemical Name:3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate
CAS No.:444118-71-2
Molecular Formula:C₃₄H₄₉N₃O₁₅Si
Molecular Weight:767.86
Hs Code.:

Synonyms:3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate

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Chemical Property of 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate

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Technology Process of 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate

There total 20 articles about 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate 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: 95.0%

: 108-24-7
acetic anhydride

: 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-L-idopyranosyluronate

: 444118-71-2
3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 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

: 444118-71-2
3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate

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: pyridine / CH₂Cl₂ / 1 h / -10 °C

8: 12.8 g / dimethylformamide / 80 °C

9: N₂H₄*H₂O; pyridine; AcOH / 0.25 h

10: 8.0 g / aq. TFA / 0.25 h

11: 68 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 6 h / 0 °C

12: 90 percent / molecular sieves 4 Angstroem; TBSOTf / CH₂Cl₂ / 1 h / -30 - 20 °C

13: 89 percent / aq. dichloroacetic acid / 3 h / 20 °C

14: 95 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 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; hydrazine hydrate; 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

Reference yield:

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

: 444118-71-2
3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate

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: pyridine / CH₂Cl₂ / 1 h / -10 °C

9: 12.8 g / dimethylformamide / 80 °C

10: N₂H₄*H₂O; pyridine; AcOH / 0.25 h

11: 8.0 g / aq. TFA / 0.25 h

12: 68 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 6 h / 0 °C

13: 90 percent / molecular sieves 4 Angstroem; TBSOTf / CH₂Cl₂ / 1 h / -30 - 20 °C

14: 89 percent / aq. dichloroacetic acid / 3 h / 20 °C

15: 95 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 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; hydrazine hydrate; 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