O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

Base Information

Chemical Name:O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose
CAS No.:114853-30-4
Molecular Formula:C₆₂H₆₇NO₂₀
Molecular Weight:1146.21
Hs Code.:

Synonyms:O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

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Chemical Property of O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

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Technology Process of O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

There total 15 articles about O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-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: 92.0%

: 220449-96-7
p-methoxybenzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 114853-30-4
O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

Guidance literature:: With ammonium nitrate; ammonium and cerium nitrate; In water; acetonitrile; at -5 ℃; for 0.0833333h;
DOI:10.1080/07328300008544072

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 114853-30-4
O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / TsOH / acetonitrile / 0.5 h / 20 °C

2: 97 percent / tetrabutylammonium bromide; diisopropylamine / CH₂Cl₂; dimethylformamide / 4 h / 20 °C

3: 74 percent / sodium cyanoborohydride; molecular sieves 3 Angstroem; HCl / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C / pH 1

4: 76 percent / molecular sieves 3 Angstroem; trimethylsilyl triflate / CH₂Cl₂ / 3 h / -70 - -30 °C

5: 92 percent / ammonium and cerium nitrate / acetonitrile; H₂O / 0.08 h / -5 °C

With ammonium nitrate; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; ammonium and cerium nitrate; tetrabutylammomium bromide; sodium cyanoborohydride; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: acetal formation / 2: Substitution / 3: Reduction / 4: glycosylation / 5: Hydrolysis;
DOI:10.1080/07328300008544072

Reference yield:

: 100-39-0
benzyl bromide

: 114853-30-4
O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / 1. (Bu₃Sn)2O 2. Bu₄NBr / toluene / 1. 4 h reflux, 2. 16h at 100 deg C

2: 33 percent / BF_3.etherate / 1,2-dichloro-ethane / 4 h / -23 °C / 4 Angstroem molecular sieves

3: 76.8 percent / MeOSO₂CF₃ / diethyl ether / 16 h / 4 Angstroem molecular sieves

4: 65.7 percent / PdCl₂ / aq. acetic acid / 16 h / ultrasonication

With boron trifluoride diethyl etherate; tetrabutylammomium bromide; bis(tri-n-butyltin)oxide; methyl trifluoromethanesulfonate; palladium dichloride; In diethyl ether; acetic acid; 1,2-dichloro-ethane; toluene;
DOI:10.1016/0008-6215(87)80279-3