p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside

Base Information

Chemical Name:p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside
CAS No.:1459246-74-2
Molecular Formula:C₄₂H₄₅NO₁₅S
Molecular Weight:835.883
Hs Code.:

Synonyms:p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside

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Chemical Property of p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside

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Technology Process of p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside

There total 2 articles about p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside 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: 70.0%

: 959862-94-3
p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

: C₁₅H₂₀Cl₃NO₉

: 1459246-74-2
p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside

Guidance literature:: p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside; C₁₅H₂₀Cl₃NO₉; In dichloromethane; at 20 ℃; for 1h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 2h; regioselective reaction; Inert atmosphere;
DOI:10.1002/open.201300024

Reference yield:

: 220645-16-9
4-methylphenyl 4,6-O-benzylidene-2-deoxyl-1-thio-2-phthalimido-β-D-glucopyranoside

: 1459246-74-2
p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: trimethylamine-borane; aluminum (III) chloride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

2.1: dichloromethane / 1 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 2 h / -40 °C / Inert atmosphere

With aluminum (III) chloride; trimethylamine-borane; In tetrahydrofuran; dichloromethane;
DOI:10.1002/open.201300024

Reference yield: 75.0%

: 1459246-74-2
p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside

: 211801-54-6,807361-40-6
p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

: 1459246-72-0
p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl(1→4)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl(1→3)]-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside; p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside; In toluene; at 20 ℃; for 1h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; silver trifluoromethanesulfonate; In toluene; at 0 ℃; for 2h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/open.201300024