phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Base Information

Chemical Name:phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide
CAS No.:302352-19-8
Molecular Formula:C₃₃H₃₅N₅O₁₃S
Molecular Weight:741.733
Hs Code.:

Synonyms:phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

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Chemical Property of phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

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Technology Process of phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

There total 1 articles about phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide 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: 76.0%

: phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronic acid

: 302352-19-8
phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Guidance literature:: With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate; In acetonitrile; at 20 ℃; for 10h;
DOI:10.1016/S0040-4020(02)00743-3

Reference yield: 74.0%

: 302352-19-8
phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

: 612844-78-7
phenyl 2-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Guidance literature:: With hydrazine; In methanol; dichloromethane; at 20 ℃; for 20h;
DOI:10.1021/ja0166693 DOI:10.1016/S0040-4020(02)00743-3

Reference yield:

: 302352-19-8
phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

: 394247-91-7
phenyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 3 steps

1: 74 percent / hydrazine / methanol; CH₂Cl₂ / 20 h / 20 °C

2: 93 percent / HATU; DIPEA / dimethylformamide / 12 h / 20 °C

3: 92 percent / DMAP; pyridine / 2 h / 20 °C

With pyridine; dmap; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; hydrazine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)00743-3