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-β-D-glucopyranoside

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-β-D-glucopyranoside
CAS No.:793672-62-5
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-β-D-glucopyranoside

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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-β-D-glucopyranoside

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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-β-D-glucopyranoside

There total 4 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-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: 90.0%

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

: 793672-57-8
4-methylphenyl 2-O-vinyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

: 793672-62-5
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-β-D-glucopyranoside

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:

: 106-45-6
para-thiocresol

: 793672-62-5
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-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 67 percent / BF₃*OEt₂ / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 97 percent / NaOMe / methanol; CH₂Cl₂ / 2.5 h / 20 °C

3: 60 percent / Na₂CO₃ / [Ir(COD)Cl]2 / toluene / 48 h / Heating

4: 90 percent / I₂; AgOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 2 h / -78 - 20 °C

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

Reference yield:

: 158852-31-4
3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose

: 793672-62-5
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-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 67 percent / BF₃*OEt₂ / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 97 percent / NaOMe / methanol; CH₂Cl₂ / 2.5 h / 20 °C

3: 60 percent / Na₂CO₃ / [Ir(COD)Cl]2 / toluene / 48 h / Heating

4: 90 percent / I₂; AgOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 2 h / -78 - 20 °C

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