(5R,6R,7R,8R)-8-azido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

Base Information

Chemical Name:(5R,6R,7R,8R)-8-azido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine
CAS No.:272124-29-5
Molecular Formula:C₂₈H₂₈N₆O₃
Molecular Weight:496.569
Hs Code.:

Synonyms:(5R,6R,7R,8R)-8-azido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

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Chemical Property of (5R,6R,7R,8R)-8-azido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

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Technology Process of (5R,6R,7R,8R)-8-azido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

There total 7 articles about (5R,6R,7R,8R)-8-azido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-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: 92.0%

: 272124-28-4
(5R,6R,7S,8R)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-[(methylsulfonyl)oxy][1,2,4]triazolo[4,3-a]pyridine

: 272124-29-5
(5R,6R,7R,8R)-8-azido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 70 ℃; for 2h;
DOI:10.1002/(SICI)1522-2675(20000315)83:3<513::AID-HLCA513>3.0.CO;2-1

Reference yield:

: 158349-24-7
(3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one

: 272124-29-5
(5R,6R,7R,8R)-8-azido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / Bu₄NBr; BCl₃ / CH₂Cl₂ / 6 h / -78 - 23 °C

2: 98 percent / pyridine / 2 h

3: 92 percent / anisyldithiophosphinic anhydride / toluene / 2 h / 25 °C

4: 76 percent / Hg(OAc)2 / tetrahydrofuran / 3 h / 23 °C

5: 100 percent / NH₃ / tetrahydrofuran; methanol / 0.5 h / 40 °C

6: 84 percent / pyridine / 0.5 h / 0 °C

7: 92 percent / NaN₃ / dimethylformamide / 2 h / 70 °C

With Lawessons reagent; pyridine; sodium azide; mercury(II) diacetate; tetrabutylammomium bromide; ammonia; boron trichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: regioselective debenzylation / 2: Acetylation / 3: Substitution / 4: Condensation / 5: Deacetylation / 6: Esterification / 7: Substitution;
DOI:10.1002/(SICI)1522-2675(20000315)83:3<513::AID-HLCA513>3.0.CO;2-1

Reference yield:

: 182074-17-5
(5R,6R,7R,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydrotriazolo[4,3-a]pyridin-8-ol

: 272124-29-5
(5R,6R,7R,8R)-8-azido-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / pyridine / 0.5 h / 0 °C

2: 92 percent / NaN₃ / dimethylformamide / 2 h / 70 °C

With pyridine; sodium azide; In N,N-dimethyl-formamide; 1: Esterification / 2: Substitution;
DOI:10.1002/(SICI)1522-2675(20000315)83:3<513::AID-HLCA513>3.0.CO;2-1