(5R,6S,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,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine
• CAS No.: 168037-63-6
• Molecular Formula: C₃₄H₃₄N₄O₄
• Molecular Weight: 562.668

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

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

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

There total 13 articles about (5R,6S,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: 82.0%

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)piperidin-2-one (158349-25-8) → (5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine (168037-63-6)

Guidance literature:

With sodium azide; trifluoromethylsulfonic anhydride; In acetonitrile; at -15 ℃; for 1h;

DOI:10.1080/00397919908085802

Reference yield: 80.0%

benzyl bromide (100-39-0) + (5R,6S,7S,8S)-7,8-bis(benzyloxy)-5-(hydroxymethyl)-5,6,7,8-tetrahydrotetrazolo<1,5-a>pyridin-6-ol → (5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine (168037-63-6)

Guidance literature:

With sodium hydride; at 60 ℃; for 5h;

DOI:10.1002/hlca.19950780221

Reference yield: 6.0%

2,3,4,6-tetra-O-benzyl-5-O-(tol-4-ylsulfonyl)-L-altrononitrile (167904-06-5) → (5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine (168037-63-6) + 2,5-anhydro-3,4,6-tri-O-benzyl-D-galactononitrile

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 100 ℃; for 16h;

DOI:10.1002/hlca.19950780221

upstream raw materials:

benzyl bromide

2,3,4,6-tetra-O-benzyl-5-O-(tol-4-ylsulfonyl)-L-altrononitrile

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

2,3-Bis-O-(phenylmethyl)-4,6-O-(phenylmethylene)-D-galactopyranose

Downstream raw materials:

[2R-(2α,3α,4α,5β)]-3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]piperidine

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