2-azidoethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside

Base Information

Chemical Name:2-azidoethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside
CAS No.:321746-79-6
Molecular Formula:C₄₁H₅₇N₃O₁₈
Molecular Weight:879.913
Hs Code.:

Synonyms:2-azidoethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside

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Chemical Property of 2-azidoethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside

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Technology Process of 2-azidoethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside

There total 6 articles about 2-azidoethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside 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: 90.0%

: (2S,3S,4S,5R,6R)-6-[(2R,3S,4S,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-benzoyloxy-6-(2-methanesulfonyloxy-ethoxy)-tetrahydro-pyran-4-yloxy]-3,4,5-tris-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 321746-79-6
2-azidoethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside

Guidance literature:: With sodium azide; 18-crown-6 ether; In N,N-dimethyl-formamide; at 20 ℃; for 50h;
DOI:10.1016/S0008-6215(00)00258-5

Reference yield:

: 201789-48-2
(2S,3S,4S,5R,6R)-6-((2R,3S,4S,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-benzoyloxy-tetrahydro-pyran-4-yloxy)-3,4,5-tris-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 321746-79-6
2-azidoethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 908 mg / LiI; NaHCO₃ / pyridine / 5 h / Heating

2: ozone / methanol; CH₂Cl₂ / -78 °C

3: NaBH₄ / 1 h / -5 °C

4: 813 mg / diethyl ether / 0 °C

5: 744 mg / Et₃N / CH₂Cl₂

6: 90 percent / 18-crown-6; NaN₃ / dimethylformamide / 50 h / 20 °C

With sodium tetrahydroborate; sodium azide; 18-crown-6 ether; sodium hydrogencarbonate; ozone; triethylamine; lithium iodide; In pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)00258-5

Reference yield:

: 321746-78-5
2-hydroxyethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside

: 321746-79-6
2-azidoethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 744 mg / Et₃N / CH₂Cl₂

2: 90 percent / 18-crown-6; NaN₃ / dimethylformamide / 50 h / 20 °C

With sodium azide; 18-crown-6 ether; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)00258-5