4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl azide

Base Information

Chemical Name:4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl azide
CAS No.:315208-33-4
Molecular Formula:C₂₈H₃₀N₄O₇
Molecular Weight:534.569
Hs Code.:

Synonyms:4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl azide

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Chemical Property of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl azide

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Technology Process of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl azide

There total 7 articles about 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-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: 95.0%

: 315208-31-2
4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl fluoride

: 315208-33-4
4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl azide

Guidance literature:: With trimethylsilylazide; In dichloromethane; at 20 ℃; for 0.0833333h;
DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b

Reference yield:

: 303082-23-7
thexyldimethylsilyl 2-deoxy-2-(dimethylmaleoylimido)-3,6-di-O-benzyl-β-D-glucopyranoside

: 315208-33-4
4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl azide

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / pyridine / 2 h / 20 °C

2: 80 percent / TBAF / tetrahydrofuran / 3 h / -20 °C

3: 93 percent / DAST / CH₂Cl₂ / -30 °C

4: 95 percent / TMSN₃ / CH₂Cl₂ / 0.08 h / 20 °C

With pyridine; trimethylsilylazide; tetrabutyl ammonium fluoride; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; dichloromethane; 1: Acetylation / 2: desilylation / 3: Substitution / 4: Substitution;
DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b

Reference yield:

: 315208-18-5
3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside

: 315208-33-4
4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl azide

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

2: 98 percent / sodium methoxide / methanol / 4 h / 20 °C

3: 85 percent / dibutyltin oxide / toluene / 3 h / Heating

4: 98 percent / pyridine / 2 h / 20 °C

5: 80 percent / TBAF / tetrahydrofuran / 3 h / -20 °C

6: 93 percent / DAST / CH₂Cl₂ / -30 °C

7: 95 percent / TMSN₃ / CH₂Cl₂ / 0.08 h / 20 °C

With pyridine; 1H-imidazole; trimethylsilylazide; tetrabutyl ammonium fluoride; sodium methylate; di(n-butyl)tin oxide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Condensation / 2: Deacetylation / 3: Etherification / 4: Acetylation / 5: desilylation / 6: Substitution / 7: Substitution;
DOI:10.1002/1099-0690(200011)2000:21<3541::aid-ejoc3541>3.3.co;2-b