(2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde

Base Information

Chemical Name:(2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde
CAS No.:857860-12-9
Molecular Formula:C₂₈H₂₉N₃O₆
Molecular Weight:503.555
Hs Code.:

Synonyms:(2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde

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Chemical Property of (2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde

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Technology Process of (2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde

There total 6 articles about (2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde 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: 46.0%

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

: (2S,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde

: 857860-12-9
(2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: With 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1021/ol0508577

Reference yield:

: (2R,3R,4S,5S)-2-Azido-6-methylene-tetrahydro-pyran-3,4,5-triol

: 857860-12-9
(2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 1.3 g / sodium hydride / dimethylformamide / 3 h / 20 °C

2: 98 percent / 1,1,1-trifluoroacetone; Oxone; sodium hydrogen carbonate / sodium EDTA / acetonitrile; H₂O / 1.5 h / 0 - 20 °C

3: 100 percent / camphorsulfonic acid / 0.17 h / 20 °C

4: 46 percent / N-methylmorpholine N-oxide / tetra-n-propyl-ammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

With Oxone; 1,1,1-trifluoro-2-propanone; camphor-10-sulfonic acid; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate; ethylene diamine tetraacetic acid tetrasodium salt; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol0508577

Reference yield:

: 857860-08-3
(5R,6R,7R,8S)-5-Azido-6,7,8-tris-benzyloxy-1,4-dioxa-spiro[2.5]octane

: 857860-12-9
(2R,3S,4R,5R,6R)-6-Azido-3,4,5-tris-benzyloxy-2-methoxy-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / camphorsulfonic acid / 0.17 h / 20 °C

2: 46 percent / N-methylmorpholine N-oxide / tetra-n-propyl-ammonium perruthenate / CH₂Cl₂ / 15 h / 20 °C

With camphor-10-sulfonic acid; 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate; In dichloromethane;
DOI:10.1021/ol0508577