2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside

Base Information

Chemical Name:2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside
CAS No.:886050-86-8
Molecular Formula:C₄₄H₅₃N₃O₉Si
Molecular Weight:796.005
Hs Code.:

Synonyms:2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside

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Chemical Property of 2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside

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Technology Process of 2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside

There total 9 articles about 2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside 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%

: 886050-90-4
2-azidoethyl 4-O-benzyl-3-O-(4-methoxybenzyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

: 123-76-2
levulinic acid

: 886050-86-8
2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1016/j.tetlet.2006.02.063

Reference yield:

: 886050-88-0
2-azidoethyl 6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

: 886050-86-8
2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: p-TsOH / acetone

2.1: NaH / dimethylformamide

3.1: trifluoroacetic acid / tetrahydrofuran / 20 °C

4.1: Bu₂SnO / toluene / 110 °C

4.2: 76 percent / Bu₄NI / toluene / Heating

5.1: 95 percent / 1,3-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂

With dmap; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/j.tetlet.2006.02.063

Reference yield:

: (3aS,4S,6R,7R,7aS)-4-(2-Azido-ethoxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

: 886050-86-8
2-azidoethyl 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-levulinoyl-3-O-(4-methoxybenzyl)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide

2.1: trifluoroacetic acid / tetrahydrofuran / 20 °C

3.1: Bu₂SnO / toluene / 110 °C

3.2: 76 percent / Bu₄NI / toluene / Heating

4.1: 95 percent / 1,3-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂

With dmap; sodium hydride; di(n-butyl)tin oxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tetlet.2006.02.063