tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-L-glycero-L-gluco-hepturonate

Base Information

Chemical Name:tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-L-glycero-L-gluco-hepturonate
CAS No.:676241-06-8
Molecular Formula:C₃₂H₃₇N₃O₆
Molecular Weight:559.662
Hs Code.:

Synonyms:tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-L-glycero-L-gluco-hepturonate

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Chemical Property of tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-L-glycero-L-gluco-hepturonate

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Technology Process of tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-L-glycero-L-gluco-hepturonate

There total 5 articles about tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-L-glycero-L-gluco-hepturonate 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:

: C₃₃H₄₀O₉S

: 676241-06-8
tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-L-glycero-L-gluco-hepturonate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 90 ℃; for 20h;
DOI:10.1016/j.tetlet.2003.12.032

Reference yield:

: 112219-66-6
(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-vinyltetrahydro-2H-pyran

: 676241-06-8
tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-L-glycero-L-gluco-hepturonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -40 °C

2.1: sodium methylate / methanol / 20 h / 20 °C

3.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 48 h / 20 °C

4.1: ozone / dichloromethane / 0.5 h / -78 °C

4.2: NaBH₄ / 11; 15 / 20 h / 20 °C

5.1: triethylamine / dichloromethane / 20 h / 20 °C

6.1: sodium azide / N,N-dimethyl-formamide / 20 h / 90 °C

With sodium azide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; acetic anhydride; ozone; triethylamine; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Zemplen deacetylation;
DOI:10.1016/j.tetlet.2003.12.032

Reference yield:

: 676241-03-5
((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol

: 676241-06-8
tert-butyl 2,6-anhydro-7-azido-3,4,5-tri-O-benzyl-7-deoxy-L-glycero-L-gluco-hepturonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 48 h / 20 °C

2.1: ozone / dichloromethane / 0.5 h / -78 °C

2.2: NaBH₄ / 11; 15 / 20 h / 20 °C

3.1: triethylamine / dichloromethane / 20 h / 20 °C

4.1: sodium azide / N,N-dimethyl-formamide / 20 h / 90 °C

With sodium azide; acetic anhydride; ozone; triethylamine; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2003.12.032