(2R,3S,4R,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-9-(p-methoxybenzyl)-1-oxa-6,9-diazaspiro<4.5>decane-7,10-dione, diacetate ester

Base Information

Chemical Name:(2R,3S,4R,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-9-(p-methoxybenzyl)-1-oxa-6,9-diazaspiro<4.5>decane-7,10-dione, diacetate ester
CAS No.:221459-82-1
Molecular Formula:C₃₆H₄₂N₂O₉Si
Molecular Weight:674.823
Hs Code.:

Synonyms:(2R,3S,4R,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-9-(p-methoxybenzyl)-1-oxa-6,9-diazaspiro<4.5>decane-7,10-dione, diacetate ester

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Chemical Property of (2R,3S,4R,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-9-(p-methoxybenzyl)-1-oxa-6,9-diazaspiro<4.5>decane-7,10-dione, diacetate ester

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Technology Process of (2R,3S,4R,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-9-(p-methoxybenzyl)-1-oxa-6,9-diazaspiro<4.5>decane-7,10-dione, diacetate ester

There total 4 articles about (2R,3S,4R,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-9-(p-methoxybenzyl)-1-oxa-6,9-diazaspiro<4.5>decane-7,10-dione, diacetate ester 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:

: 221459-60-5
(2S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione

: 221459-82-1
(2R,3S,4R,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-9-(p-methoxybenzyl)-1-oxa-6,9-diazaspiro<4.5>decane-7,10-dione, diacetate ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) OsO₄, pyridine, 2.) pyridine, DMAP / 1.) THF, 0 deg C to room temp., 4 h, 2.) CH₂Cl₂, overnight

2: 92 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 0.33 h

3: 1.) NH₃, 2.) pyridinium p-toluenesulfonate / 1.) CH₃OH, CHCl₃, 2.) C₆H₆, room temp., 24 h

With pyridine; dmap; osmium(VIII) oxide; ammonia; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1021/jo982259u

Reference yield:

: 2-(tert-butyl-diphenyl-silanyloxymethyl)-7-(4-methoxy-benzyl)-4-phenylselanyl-1-oxa-7-aza-spiro[4.4]nonane-6,9-dione

: 221459-82-1
(2R,3S,4R,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-9-(p-methoxybenzyl)-1-oxa-6,9-diazaspiro<4.5>decane-7,10-dione, diacetate ester

Guidance literature:: Multi-step reaction with 4 steps

1: NaIO₄, NaHCO₃ / methanol / 12 h / 0 °C

2: 1.) OsO₄, pyridine, 2.) pyridine, DMAP / 1.) THF, 0 deg C to room temp., 4 h, 2.) CH₂Cl₂, overnight

3: 92 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 0.33 h

4: 1.) NH₃, 2.) pyridinium p-toluenesulfonate / 1.) CH₃OH, CHCl₃, 2.) C₆H₆, room temp., 24 h

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; ammonia; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;
DOI:10.1021/jo982259u

Reference yield:

: 221459-66-1
(2R,3S,4R,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>nonane-6,9-dione, diacetate ester

: 221459-82-1
(2R,3S,4R,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-9-(p-methoxybenzyl)-1-oxa-6,9-diazaspiro<4.5>decane-7,10-dione, diacetate ester

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 0.33 h

2: 1.) NH₃, 2.) pyridinium p-toluenesulfonate / 1.) CH₃OH, CHCl₃, 2.) C₆H₆, room temp., 24 h

With ammonia; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1021/jo982259u