(5R,6R,7R,8R)-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,8R)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine
CAS No.:168037-66-9
Molecular Formula:C₂₉H₃₁N₅O₄
Molecular Weight:513.596
Hs Code.:

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

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

There total 6 articles about (5R,6R,7R,8R)-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: 40.0%

: 208592-90-9
N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-oxo-piperidin-3-yl)-acetamide

: 8-acetamido-5-<(benzyloxy)methyl>tetrazolo<1,5-a>pyridine

: 168037-66-9
(5R,6R,7R,8R)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine

: 167904-24-7
(5R,6R,7R,8S)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine

Guidance literature:: With trimethylsilylazide; phosphorus pentachloride; In acetonitrile; at 15 ℃; for 24h;
DOI:10.1080/00397919908085802

Reference yield: 10.0%

: 167904-23-6
2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-5-O-(tol-4-ylsulfonyl)-L-idononitrile

: 168037-66-9
(5R,6R,7R,8R)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine

: 167904-24-7
(5R,6R,7R,8S)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine

Guidance literature:: With sodium azide; In methanol; water; for 16h; Yields of byproduct given; Heating;
DOI:10.1002/hlca.19950780221

Reference yield:

: 168037-65-8
(E)-2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucose oxime

: 168037-66-9
(5R,6R,7R,8R)-8-acetamido-6,7-bis(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine

Guidance literature:: Multi-step reaction with 5 steps

1: 36 percent / PPh₃, CBr₄, pyridine / acetonitrile; tetrahydrofuran / 35 h / Ambient temperature

2: 97 percent / pyridine*SO₃, Et₃N / dimethylsulfoxide / 1.08 h / Ambient temperature

3: NaBH₄, CeCl₃*6H₂O / methanol / 22 h / -40 - -20 °C

4: 85 percent / pyridine / 4.5 h / 55 - 60 °C

5: 10 percent / NaN₃ / methanol; H₂O / 16 h / Heating

With pyridine; sodium tetrahydroborate; sodium azide; cerium(III) chloride; carbon tetrabromide; sulfur trioxide pyridine complex; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1002/hlca.19950780221