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

Base Information

• Chemical Name: (5R,6R,7R,8S)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine
• CAS No.: 167904-24-7
• Molecular Formula: C₂₉H₃₁N₅O₄
• Molecular Weight: 513.596

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

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

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

There total 9 articles about (5R,6R,7R,8S)-8-acetamido-6,7-bis(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: 75.0%

2-acetamido-5-azido-3,4,6-tri-O-benzyl-2,5-dideoxy-D-glucononitrile (167904-28-1) → (Z)-2-acetamido-5-azido-4,6-di-O-benzyl-2,3,5-trideoxy-D-erythro-hex-2-enononitrile + (5R,6R,7R,8S)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine (167904-24-7)

Guidance literature:

at 120 - 130 ℃; for 2h;

DOI:10.1002/hlca.19950780221

Reference yield: 45.0%

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-5-O-(tol-4-ylsulfonyl)-L-idononitrile (167904-23-6) → 2-acetamido-5-azido-3,4,6-tri-O-benzyl-2,5-dideoxy-D-glucononitrile (167904-28-1) + (5S,6R,7R,8S)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydrotetrazolo<1,5-a>pyridine + (5R,6R,7R,8S)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine (167904-24-7)

Guidance literature:

With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; at 60 - 65 ℃; for 28h;

DOI:10.1002/hlca.19950780221

Reference yield: 40.0%

N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-oxo-piperidin-3-yl)-acetamide (208592-90-9) → 8-acetamido-5-<(benzyloxy)methyl>tetrazolo<1,5-a>pyridine + (5R,6R,7R,8R)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine (168037-66-9) + (5R,6R,7R,8S)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine (167904-24-7)

Guidance literature:

With trimethylsilylazide; phosphorus pentachloride; In acetonitrile; at 15 ℃; for 24h;

DOI:10.1080/00397919908085802

upstream raw materials:

2-acetamido-5-azido-3,4,6-tri-O-benzyl-2,5-dideoxy-D-glucononitrile

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-5-O-(tol-4-ylsulfonyl)-L-idononitrile

N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-oxo-piperidin-3-yl)-acetamide

(E)-2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucose oxime

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