(1R,2R,4R,6S)-1-(benzyloxycarbonylamino)-6-(hydroxymethyl)bicyclo[2.2.2]octane-2-ol

Base Information

Chemical Name:(1R,2R,4R,6S)-1-(benzyloxycarbonylamino)-6-(hydroxymethyl)bicyclo[2.2.2]octane-2-ol
CAS No.:1391829-32-5
Molecular Formula:C₁₇H₂₃NO₄
Molecular Weight:305.374
Hs Code.:

Synonyms:(1R,2R,4R,6S)-1-(benzyloxycarbonylamino)-6-(hydroxymethyl)bicyclo[2.2.2]octane-2-ol

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Chemical Property of (1R,2R,4R,6S)-1-(benzyloxycarbonylamino)-6-(hydroxymethyl)bicyclo[2.2.2]octane-2-ol

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Technology Process of (1R,2R,4R,6S)-1-(benzyloxycarbonylamino)-6-(hydroxymethyl)bicyclo[2.2.2]octane-2-ol

There total 3 articles about (1R,2R,4R,6S)-1-(benzyloxycarbonylamino)-6-(hydroxymethyl)bicyclo[2.2.2]octane-2-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: 62.0%

: 1391829-30-3
(1R,3S,6R,7R)-7-(benzyloxycarbonylamino)-4-oxa-8-tricyclo[4.3.1.0(3,7)]decan-5-one

: 1391829-32-5
(1R,2R,4R,6S)-1-(benzyloxycarbonylamino)-6-(hydroxymethyl)bicyclo[2.2.2]octane-2-ol

Guidance literature:: With sodium tetrahydroborate; In water; isopropyl alcohol; at 20 ℃; for 48h;
DOI:10.1007/s00726-011-1097-6

Reference yield:

: 1092566-98-7
(1R,2R,3R,6R,7R)-7-(benzyloxycarbonylamino)-2-iodo-4-oxa-8-tricyclo[4.3.1.0(3,7)]decan-5-one

: 1391829-32-5
(1R,2R,4R,6S)-1-(benzyloxycarbonylamino)-6-(hydroxymethyl)bicyclo[2.2.2]octane-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / 80 °C / Microwave irradiation; Inert atmosphere

2: sodium tetrahydroborate / water; isopropyl alcohol / 48 h / 20 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In water; isopropyl alcohol; toluene;
DOI:10.1007/s00726-011-1097-6

Reference yield:

: (1S,2R,4R)-1-(benzyloxycarbonylamino)bicyclo[2.2.2]oct-5-ene-2-carboxylic acid

: 1391829-32-5
(1R,2R,4R,6S)-1-(benzyloxycarbonylamino)-6-(hydroxymethyl)bicyclo[2.2.2]octane-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1: iodine; sodium hydrogencarbonate; potassium iodide / dichloromethane; water

2: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / 80 °C / Microwave irradiation; Inert atmosphere

3: sodium tetrahydroborate / water; isopropyl alcohol / 48 h / 20 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium iodide; In dichloromethane; water; isopropyl alcohol; toluene;
DOI:10.1007/s00726-011-1097-6