O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranose

Base Information

Chemical Name:O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranose
CAS No.:162710-61-4
Molecular Formula:C₂₃H₃₁N₃O₁₀
Molecular Weight:509.513
Hs Code.:

Synonyms:O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranose

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Chemical Property of O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranose

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Technology Process of O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranose

There total 7 articles about O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranose 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:

: 93793-97-6
1,6-anhydro-2,3-O-endo-(4-methoxybenzylidene)-β-D-mannopyranose

: 162710-61-4
O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: 68 percent / trimethylsilyl triflate, 4 Angstroem molecular sieves / CH₂Cl₂ / 1.) -20 deg C, 2 h, 2.) -20 deg C to r.t., 1 h

2: 66 percent / TFA, NaBH₃CN, 3 Angstroem molecular sieves / dimethylformamide / 24 h / Ambient temperature

3: pyridine / CH₂Cl₂ / 1.) -10 deg C, 10 min, 2.) r.t., 1 h

4: NaN₃ / dimethylformamide / 18 h / Ambient temperature

5: 84 percent / NaOMe / methanol / 15 h / Ambient temperature

6: 1.) dibutyltin oxide, 3 Angstroem molecular sieves, 2.) N-methylimidazole / 1.) CH₃CN, 80 deg C, 2 h, 2.) 3.5 h

With pyridine; 1-methyl-1H-imidazole; sodium azide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; di(n-butyl)tin oxide; sodium cyanoborohydride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00111a008

Reference yield:

: 203435-09-0
2,3,4,6-tetra-O-benzoyl-α,b-D-galactopyranosyl trichloroacetimidate

: 162710-61-4
O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: 68 percent / trimethylsilyl triflate, 4 Angstroem molecular sieves / CH₂Cl₂ / 1.) -20 deg C, 2 h, 2.) -20 deg C to r.t., 1 h

2: 66 percent / TFA, NaBH₃CN, 3 Angstroem molecular sieves / dimethylformamide / 24 h / Ambient temperature

3: pyridine / CH₂Cl₂ / 1.) -10 deg C, 10 min, 2.) r.t., 1 h

4: NaN₃ / dimethylformamide / 18 h / Ambient temperature

5: 84 percent / NaOMe / methanol / 15 h / Ambient temperature

6: 1.) dibutyltin oxide, 3 Angstroem molecular sieves, 2.) N-methylimidazole / 1.) CH₃CN, 80 deg C, 2 h, 2.) 3.5 h

With pyridine; 1-methyl-1H-imidazole; sodium azide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; di(n-butyl)tin oxide; sodium cyanoborohydride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00111a008

Reference yield:

: 162710-59-0
O-(2,3,4,6-Tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranose

: 162710-61-4
O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-3-O-(4-methoxybenzyl)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / NaOMe / methanol / 15 h / Ambient temperature

2: 1.) dibutyltin oxide, 3 Angstroem molecular sieves, 2.) N-methylimidazole / 1.) CH₃CN, 80 deg C, 2 h, 2.) 3.5 h

With 1-methyl-1H-imidazole; 3 A molecular sieve; sodium methylate; di(n-butyl)tin oxide; In methanol;
DOI:10.1021/jo00111a008