4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)ethyl)-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)ethyl)-1-thio-α-D-mannopyranoside
CAS No.:793672-58-9
Molecular Formula:C₄₈H₅₇IO₁₁S
Molecular Weight:968.944
Hs Code.:

Synonyms:4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)ethyl)-1-thio-α-D-mannopyranoside

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Chemical Property of 4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)ethyl)-1-thio-α-D-mannopyranoside

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Technology Process of 4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)ethyl)-1-thio-α-D-mannopyranoside

There total 5 articles about 4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)ethyl)-1-thio-α-D-mannopyranoside 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: 86.0%

: 4064-06-6
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

: 793672-51-2
4-methylphenyl 2-O-vinyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

: 793672-58-9
4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)ethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; iodine; silver trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; for 2h;
DOI:10.1021/ol048427o

Reference yield:

: 146864-77-9
3,4,6-tri-O-benzyl-1,2-O-(exo-methoxyethylidene)-β-D-mannopyranose

: 793672-58-9
4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)ethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / 1,2-dichloro-ethane / 72 h / Heating

2: 100 percent / NaOMe / methanol; CH₂Cl₂ / 24 h / 20 °C

3: 78 percent / Na₂CO₃ / [Ir(COD)Cl]2 / toluene / 60 h / Heating

4: 86 percent / I₂; AgOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 2 h / -78 - 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; iodine; sodium methylate; silver trifluoromethanesulfonate; sodium carbonate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; In methanol; dichloromethane; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ol048427o

Reference yield:

: 106-45-6
para-thiocresol

: 793672-58-9
4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-O-yl)ethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / 1,2-dichloro-ethane / 72 h / Heating

2: 100 percent / NaOMe / methanol; CH₂Cl₂ / 24 h / 20 °C

3: 78 percent / Na₂CO₃ / [Ir(COD)Cl]2 / toluene / 60 h / Heating

4: 86 percent / I₂; AgOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 2 h / -78 - 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; iodine; sodium methylate; silver trifluoromethanesulfonate; sodium carbonate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; In methanol; dichloromethane; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ol048427o