(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine

Base Information

• Chemical Name: (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine
• CAS No.: 139189-64-3
• Molecular Formula: C₃₄H₃₄N₄O₄
• Molecular Weight: 562.668

Synonyms:(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine

Chemical Property of (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine

Chemical Property:

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Technology Process of (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine

There total 8 articles about (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine 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: 87.0%

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one (77174-08-4) → (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine (139189-64-3) + (3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>-1-(trifluoromethyl-sulfonyl)pireridin-2-one

Guidance literature:

With sodium azide; trifluoromethylsulfonic anhydride; In acetonitrile; at -15 ℃; for 0.833333h;

DOI:10.1080/00397919908085802

Reference yield: 70.0%

2,3,4,6-tetra-O-benzyl-5-O-(4-toluenesulfonyl)-L-idononitrile (139189-63-2) → 2,3,5-tri-O-benzyl-β-D-arabinofuranosyl cyanide (52492-43-0) + (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine (139189-64-3)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 110 - 120 ℃; for 3.25h;

DOI:10.1002/hlca.19910740839

Reference yield: 43.0%

2,3,4,6-tetra-O-benzyl-5-bromo-5-deoxy-L-idononitrile (139189-58-5) → (Z)-(2S,3R)-2,3,4,6-Tetrakis-benzyloxy-hex-4-enenitrile + (E)-(2S,3S,4R)-2,3,4,6-Tetrakis-benzyloxy-hex-5-enenitrile + (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine (139189-64-3)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 110 - 125 ℃; for 4h;

DOI:10.1002/hlca.19910740839

upstream raw materials:

2,3,4,6-tetra-O-benzyl-5-bromo-5-deoxy-L-idononitrile

2,3,4,6-tetra-O-benzyl-5-O-(4-toluenesulfonyl)-L-idononitrile

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol

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