3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-cyclopentylidene-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 3-O-benzyl-1,2-O-cyclopentylidene-β-L-idopyranosyluronate
• CAS No.: 444118-55-2
• Molecular Formula: C₃₅H₅₁N₃O₁₃Si
• Molecular Weight: 749.888
• Mol file: 444118-55-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-cyclopentylidene-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: 88.0%

methyl 3-O-benzyl-1,2-O-cyclopentylidene-β-L-idopyranosyluronate (444118-45-0) + 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate → 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-cyclopentylidene-β-L-idopyranosyluronate (444118-55-2)

Guidance literature:

With 4 A molecular sieve; t-butyldimethylsiyl triflate; In dichloromethane; at -78 - 20 ℃;

DOI:10.1002/1521-3773(20020617)41:12<2128::AID-ANIE2128>3.0.CO;2-V

Reference yield:

methyl 3-O-benzyl-L-idopyranosyluronate (87326-77-0,87326-78-1) → 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-cyclopentylidene-β-L-idopyranosyluronate (444118-55-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 0 - 20 °C

2: 88 percent / molecular sieves 4 Angstroem; TBSOTf / CH₂Cl₂ / 1 h / -30 - 20 °C

With 4 A molecular sieve; t-butyldimethylsiyl triflate; (+)-10-camphorsulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

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) → 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-cyclopentylidene-β-L-idopyranosyluronate (444118-55-2)

Guidance literature:

Multi-step reaction with 12 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: 56 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 0 - 20 °C

12: 88 percent / molecular sieves 4 Angstroem; TBSOTf / CH₂Cl₂ / 1 h / -30 - 20 °C

With pyridine; 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

upstream raw materials:

methyl 3-O-benzyl-1,2-O-cyclopentylidene-β-L-idopyranosyluronate

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

benzyl bromide

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

Downstream raw materials:

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

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