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-L-idopyranosyl acetate

Base Information

Chemical Name: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-L-idopyranosyl acetate
CAS No.:676342-76-0
Molecular Formula:C₅₁H₄₉N₃O₁₅
Molecular Weight:943.961
Hs Code.:

Synonyms: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-L-idopyranosyl acetate

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Chemical Property of 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-L-idopyranosyl acetate

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Technology Process of 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-L-idopyranosyl acetate

There total 8 articles about 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-L-idopyranosyl acetate 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: 89.0%

: 108-24-7
acetic anhydride

: 676342-75-9
1,6-anhydro-4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-benzoyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside

: 676342-76-0
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-L-idopyranosyl acetate

Guidance literature:: With trifluoroacetic acid; at 20 ℃; for 24h;
DOI:10.1002/chem.200305096

Reference yield:

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

: 676342-76-0
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-L-idopyranosyl acetate

Guidance literature:: Multi-step reaction with 8 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

With pyridine; hydrogenchloride; triethylsilane; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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

: 676342-76-0
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-L-idopyranosyl acetate

Guidance literature:: Multi-step reaction with 9 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

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