3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonamide

Base Information

Chemical Name:3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonamide
CAS No.:1426550-78-8
Molecular Formula:C₄₀H₄₄N₂O₆
Molecular Weight:648.799
Hs Code.:

Synonyms:3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonamide

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Chemical Property of 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonamide

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Technology Process of 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonamide

There total 9 articles about 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonamide 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%

: 1426550-77-7
3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonic acid

: 1426550-78-8
3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonamide

Guidance literature:: With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1002/ejoc.201200923

Reference yield:

: 1426550-59-5
2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-L-iditol

: 1426550-78-8
3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonamide

Guidance literature:: Multi-step reaction with 7 steps

1: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / Inert atmosphere

3: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

4: trimethylphosphane / methanol; toluene / 3 h / 0 °C / Inert atmosphere

5: methanol / 0 - 5 °C / Inert atmosphere

6: hydrogenchloride / tetrahydrofuran; water / 20 h

7: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With hydrogenchloride; methanol; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; chloroformic acid ethyl ester; Dess-Martin periodane; triethylamine; triphenylphosphine; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 5: |Ugi Condensation;
DOI:10.1002/ejoc.201200923

Reference yield:

: 5-azido-2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-D-glucitol

: 1426550-78-8
3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonamide

Guidance literature:: Multi-step reaction with 6 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / Inert atmosphere

2: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

3: trimethylphosphane / methanol; toluene / 3 h / 0 °C / Inert atmosphere

4: methanol / 0 - 5 °C / Inert atmosphere

5: hydrogenchloride / tetrahydrofuran; water / 20 h

6: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With hydrogenchloride; methanol; tetrabutyl ammonium fluoride; chloroformic acid ethyl ester; Dess-Martin periodane; triethylamine; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 4: |Ugi Condensation;
DOI:10.1002/ejoc.201200923