((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

Base Information

Chemical Name:((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol
CAS No.:676241-15-9
Molecular Formula:C₂₈H₃₁N₃O₅
Molecular Weight:489.571
Hs Code.:

Synonyms:((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

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Chemical Property of ((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

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Technology Process of ((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

There total 5 articles about ((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol 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: 62.0%

: 676241-14-8
(2R,3R,4R,5S,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran

: 676241-15-9
((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

Guidance literature:: (2R,3R,4R,5S,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran; With ozone; In dichloromethane; at -78 ℃; for 0.5h;

With sodium tetrahydroborate; In methanol; dichloromethane; at 20 ℃; for 20h; Further stages.;
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

: 676241-15-9
((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

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

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

5.2: NaBH₄ / 11; 15 / 20 h / 20 °C

With sodium azide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; ozone; triethylamine; 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

: 676241-15-9
((2S,3S,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

3.2: NaBH₄ / 11; 15 / 20 h / 20 °C

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