(1R,4R,7R,8R)-8-Benzyloxy-5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-7-ol

Base Information

Chemical Name:(1R,4R,7R,8R)-8-Benzyloxy-5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-7-ol
CAS No.:212695-14-2
Molecular Formula:C₂₀H₂₃NO₅S
Molecular Weight:389.472
Hs Code.:

Synonyms:(1R,4R,7R,8R)-8-Benzyloxy-5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-7-ol

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Chemical Property of (1R,4R,7R,8R)-8-Benzyloxy-5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-7-ol

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Technology Process of (1R,4R,7R,8R)-8-Benzyloxy-5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-7-ol

There total 8 articles about (1R,4R,7R,8R)-8-Benzyloxy-5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-7-ol 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: 94.0%

: 212695-12-0
Toluene-4-sulfonic acid (2R,3S,4R,5R)-4-benzyloxy-3-hydroxy-5-(toluene-4-sulfonylamino)-tetrahydro-pyran-2-ylmethyl ester

: 212695-14-2
(1R,4R,7R,8R)-8-Benzyloxy-5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-7-ol

Guidance literature:: With sodium hydroxide; In dimethyl sulfoxide; for 24h; Ambient temperature;
DOI:10.1139/cjc-76-4-431

Reference yield:

: 100-39-0
benzyl bromide

: 212695-14-2
(1R,4R,7R,8R)-8-Benzyloxy-5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-7-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH, 2.) Bu₄NI / 1.) THF, RT, 30 min, 2.) THF, RT, 12 h

2: 97 percent / 1percent HCl/MeOH / 1.5 h / Ambient temperature

3: H₂ / 10percent Pd/C / methanol / 0.75 h / 310.3 Torr / Ambient temperature

4: pyridine / 12 h / Ambient temperature

5: 94 percent / aq. NaOH / dimethylsulfoxide / 24 h / Ambient temperature

With pyridine; hydrogenchloride; methanol; sodium hydroxide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; palladium on activated charcoal; In methanol; dimethyl sulfoxide;
DOI:10.1139/cjc-76-4-431

Reference yield:

: 212695-05-1
1,5-anhydro-2-azido-2-deoxy-4,6-O-benzylidene-D-mannitol

: 212695-14-2
(1R,4R,7R,8R)-8-Benzyloxy-5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-7-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH, 2.) Bu₄NI / 1.) THF, RT, 30 min, 2.) THF, RT, 12 h

2: 97 percent / 1percent HCl/MeOH / 1.5 h / Ambient temperature

3: H₂ / 10percent Pd/C / methanol / 0.75 h / 310.3 Torr / Ambient temperature

4: pyridine / 12 h / Ambient temperature

5: 94 percent / aq. NaOH / dimethylsulfoxide / 24 h / Ambient temperature

With pyridine; hydrogenchloride; methanol; sodium hydroxide; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; palladium on activated charcoal; In methanol; dimethyl sulfoxide;
DOI:10.1139/cjc-76-4-431