methyl 6-O-acetyl-4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-benzoyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside

Base Information

Chemical Name:methyl 6-O-acetyl-4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-benzoyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside
CAS No.:676342-78-2
Molecular Formula:C₅₀H₄₉N₃O₁₄
Molecular Weight:915.951
Hs Code.:

Synonyms:methyl 6-O-acetyl-4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-benzoyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside

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Chemical Property of methyl 6-O-acetyl-4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-benzoyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside

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Technology Process of methyl 6-O-acetyl-4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-benzoyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside

There total 11 articles about methyl 6-O-acetyl-4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-benzoyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside 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:

: 81562-09-6
6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside

: 676342-78-2
methyl 6-O-acetyl-4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-benzoyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: 88 percent / HCl / ethanol / 18 h / 95 °C

2: 98 percent / Et₃N / CH₂Cl₂ / 3.5 h / 20 °C

3: TMSOTf; 3 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -78 °C

4: Et₃SiH / CH₂Cl₂ / 1 h

5: 181 mg / tetra-n-butylammonium fluoride / CH₂Cl₂; tetrahydrofuran / 1.5 h

6: 85 percent / pyridine / CH₂Cl₂ / 4 h / cooling

7: 58 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

8: 89 percent / CF₃COOH / 24 h / 20 °C

9: 82 percent / HBr; AcOH; Ac₂O / CH₂Cl₂ / 0.5 h / 20 °C

10: K₂CO₃; 4 Angstroem molecular sieves / CH₂Cl₂ / 8 h / -78 - 20 °C

11: 58 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

With pyridine; hydrogenchloride; triethylsilane; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen bromide; acetic anhydride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1002/chem.200305096

Reference yield:

: 87357-54-8
6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose

: 676342-78-2
methyl 6-O-acetyl-4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-benzoyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside

Guidance literature:: Multi-step reaction with 12 steps

1.1: BH₃*THF / tetrahydrofuran / 3 h / 20 °C

1.2: 92 percent / aq. H₂O₂; NaOH / tetrahydrofuran

2.1: 88 percent / HCl / ethanol / 18 h / 95 °C

3.1: 98 percent / Et₃N / CH₂Cl₂ / 3.5 h / 20 °C

4.1: TMSOTf; 3 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -78 °C

5.1: Et₃SiH / CH₂Cl₂ / 1 h

6.1: 181 mg / tetra-n-butylammonium fluoride / CH₂Cl₂; tetrahydrofuran / 1.5 h

7.1: 85 percent / pyridine / CH₂Cl₂ / 4 h / cooling

8.1: 58 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

9.1: 89 percent / CF₃COOH / 24 h / 20 °C

10.1: 82 percent / HBr; AcOH; Ac₂O / CH₂Cl₂ / 0.5 h / 20 °C

11.1: K₂CO₃; 4 Angstroem molecular sieves / CH₂Cl₂ / 8 h / -78 - 20 °C

12.1: 58 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

With pyridine; hydrogenchloride; triethylsilane; borane-THF; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen bromide; acetic anhydride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1002/chem.200305096

Reference yield:

: 60619-47-8
1,6-anhydro-β-L-idopyranose

: 676342-78-2
methyl 6-O-acetyl-4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-benzoyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-α-L-idopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / Et₃N / CH₂Cl₂ / 3.5 h / 20 °C

2: TMSOTf; 3 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -78 °C

3: Et₃SiH / CH₂Cl₂ / 1 h

4: 181 mg / tetra-n-butylammonium fluoride / CH₂Cl₂; tetrahydrofuran / 1.5 h

5: 85 percent / pyridine / CH₂Cl₂ / 4 h / cooling

6: 58 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

7: 89 percent / CF₃COOH / 24 h / 20 °C

8: 82 percent / HBr; AcOH; Ac₂O / CH₂Cl₂ / 0.5 h / 20 °C

9: K₂CO₃; 4 Angstroem molecular sieves / CH₂Cl₂ / 8 h / -78 - 20 °C

10: 58 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

With pyridine; triethylsilane; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen bromide; acetic anhydride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200305096