2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide

Base Information

Chemical Name:2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide
CAS No.:147158-07-4
Molecular Formula:C₃₈H₄₃N₅O₁₆
Molecular Weight:825.783
Hs Code.:

Synonyms:2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide

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Chemical Property of 2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide

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Technology Process of 2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide

There total 8 articles about 2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide 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: 83.0%

: 70831-94-6
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

: 147157-96-8
2-acetamido-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide

: 147158-07-4
2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide

Guidance literature:: With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; In nitromethane; at -10 ℃;
DOI:10.1002/prac.19923340705

Reference yield: 34.0%

: 87190-67-8
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate

: 147157-96-8
2-acetamido-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide

: 147158-07-4
2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide

Guidance literature:: With boron trifluoride diethyl etherate; In methanol; dichloromethane; at 20 ℃; for 16h;
DOI:10.1021/ol025627w

Reference yield:

: 85-44-9
phthalic anhydride

: 147158-07-4
2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaOMe / methanol / 0.17 h / 20 °C

1.2: Et₃N / methanol / 0.67 h / 20 - 50 °C

1.3: 40 percent / pyridine / 16 h / 20 °C

2.1: 78.9 percent / SnCl₄ / CH₂Cl₂ / 16 h / 20 °C

3.1: 90.3 percent / N-bromosuccinamide / acetone; H₂O / 1 h / 20 °C

4.1: 57 percent / K₂CO₃ / CH₂Cl₂ / 18 h / 20 °C

5.1: 34 percent / borontrifluoride diethyletherate / methanol; CH₂Cl₂ / 16 h / 20 °C

With N-bromosuccinamide; boron trifluoride diethyl etherate; sodium methylate; tin(IV) chloride; potassium carbonate; In methanol; dichloromethane; water; acetone;
DOI:10.1021/ol025627w