1-benzyloxymethyl-2,5-dihydro-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione

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Chemical Name:1-benzyloxymethyl-2,5-dihydro-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione
CAS No.:856414-24-9
Molecular Formula:C₅₃H₄₉N₃O₈
Molecular Weight:855.987
Hs Code.:

Synonyms:1-benzyloxymethyl-2,5-dihydro-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione

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Chemical Property of 1-benzyloxymethyl-2,5-dihydro-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione

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Technology Process of 1-benzyloxymethyl-2,5-dihydro-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione

There total 4 articles about 1-benzyloxymethyl-2,5-dihydro-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione 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: 64.0%

: 856414-22-7
1-benzyloxymethyl-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrolidine-2,5-dione

: 856414-24-9
1-benzyloxymethyl-2,5-dihydro-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20 ℃; for 48h;
DOI:10.1016/j.tet.2005.03.101

Reference yield:

: 856414-21-6
3-bromo-1-benzyloxymethyl-2,5-dihydro-4-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione

: 856414-24-9
1-benzyloxymethyl-2,5-dihydro-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 46 percent / hydrogen; NaHCO₃ / Pd/C / ethyl acetate / 24 h / 20 °C / 750.06 Torr

2: 64 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / dioxane / 48 h / 20 °C

With hydrogen; sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In 1,4-dioxane; ethyl acetate;
DOI:10.1016/j.tet.2005.03.101

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 856414-24-9
1-benzyloxymethyl-2,5-dihydro-3-[1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-pyrrole-2,5-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 64 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / -78 - 20 °C

2: 46 percent / hydrogen; NaHCO₃ / Pd/C / ethyl acetate / 24 h / 20 °C / 750.06 Torr

3: 64 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / dioxane / 48 h / 20 °C

With di-isopropyl azodicarboxylate; hydrogen; sodium hydrogencarbonate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethyl acetate; 1: Mitsunobu reaction;
DOI:10.1016/j.tet.2005.03.101