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

Base Information

Chemical Name: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
CAS No.:676342-75-9
Molecular Formula:C₄₇H₄₃N₃O₁₂
Molecular Weight:841.871
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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: 58.0%

: 334834-19-4
1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside

: C₂₉H₂₅Cl₃N₄O₇

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

: 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

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -78 - 20 ℃;
DOI:10.1002/chem.200305096

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

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

: 676342-75-9
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

Guidance literature:: Multi-step reaction with 8 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

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