p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside
CAS No.:868618-88-6
Molecular Formula:C₁₉H₂₃N₃O₇S
Molecular Weight:437.474
Hs Code.:

Synonyms:p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside

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Chemical Property of p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside

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Technology Process of p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside

There total 3 articles about p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-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: 87.0%

: 185114-94-7,155417-78-0
1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

: 106-45-6
para-thiocresol

: 868618-88-6
p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 40 ℃; for 12h; chemoselective reaction;
DOI:10.1016/j.tet.2015.11.029

Reference yield: 54.0%

: 13964-23-3
3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose

: 108-24-7
acetic anhydride

: 106-45-6
para-thiocresol

: 868618-88-6
p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: 3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose; With hydrogenchloride; In water; at 20 ℃; for 16h;

acetic anhydride; With pyridine; dmap; at 0 - 20 ℃;

para-thiocresol; With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 6h;
DOI:10.1002/anie.201915913

Reference yield:

: 27581-57-3
3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 868618-88-6
p-methylphenyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: HCl / dioxane / 1 h / 20 °C

1.2: 94 percent / 4-(dimethylamino)pyridine; pyridine / 2 h / 20 °C

2.1: 34.3 percent / boron trifluoride diethyl etherate / CH₂Cl₂ / 20 °C

With hydrogenchloride; boron trifluoride diethyl etherate; In 1,4-dioxane; dichloromethane;
DOI:10.1016/j.bmc.2005.05.058