8-<(1S,2S)-3-hydroxy-1-methylenepropyl>-3-methyl-6,9-bis(p-methoxybenzyl)-3,4,8-trihydroxy-6,9-diaza-1-oxaspiro<4.5>decane-7,10-dione

Base Information

Chemical Name:8-<(1S,2S)-3-hydroxy-1-methylenepropyl>-3-methyl-6,9-bis(p-methoxybenzyl)-3,4,8-trihydroxy-6,9-diaza-1-oxaspiro<4.5>decane-7,10-dione
CAS No.:117183-97-8
Molecular Formula:C₂₈H₃₄N₂O₉
Molecular Weight:542.586
Hs Code.:

Synonyms:8-<(1S,2S)-3-hydroxy-1-methylenepropyl>-3-methyl-6,9-bis(p-methoxybenzyl)-3,4,8-trihydroxy-6,9-diaza-1-oxaspiro<4.5>decane-7,10-dione

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Chemical Property of 8-<(1S,2S)-3-hydroxy-1-methylenepropyl>-3-methyl-6,9-bis(p-methoxybenzyl)-3,4,8-trihydroxy-6,9-diaza-1-oxaspiro<4.5>decane-7,10-dione

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Technology Process of 8-<(1S,2S)-3-hydroxy-1-methylenepropyl>-3-methyl-6,9-bis(p-methoxybenzyl)-3,4,8-trihydroxy-6,9-diaza-1-oxaspiro<4.5>decane-7,10-dione

There total 7 articles about 8-<(1S,2S)-3-hydroxy-1-methylenepropyl>-3-methyl-6,9-bis(p-methoxybenzyl)-3,4,8-trihydroxy-6,9-diaza-1-oxaspiro<4.5>decane-7,10-dione 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: 25.0%

: 95694-70-5
(1S,6R)-6-hydroxy-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

: 117183-95-6
(1S,6R)-6-hydroxy-7,9-bis(p-methoxybenzyl)-1-<(1S,2S)-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

: 117183-97-8
8-<(1S,2S)-3-hydroxy-1-methylenepropyl>-3-methyl-6,9-bis(p-methoxybenzyl)-3,4,8-trihydroxy-6,9-diaza-1-oxaspiro<4.5>decane-7,10-dione

Guidance literature:: With acetic acid; for 33h; Ambient temperature;
DOI:10.1021/jo00261a009

Reference yield:

: 95237-55-1
(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

: 117183-97-8
8-<(1S,2S)-3-hydroxy-1-methylenepropyl>-3-methyl-6,9-bis(p-methoxybenzyl)-3,4,8-trihydroxy-6,9-diaza-1-oxaspiro<4.5>decane-7,10-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 49 percent / CAN / acetonitrile / 0.42 h

2: 100 percent / PPTS / acetone / 12 h / Ambient temperature

3: 1.) NaH / 1.) DMF, 2.) 2 h

4: 90 percent / Bu₄NF / CH₂Cl₂; tetrahydrofuran / 0.5 h / 25 °C

5: 78 percent / DDQ, H₂O / CH₂Cl₂ / 2 h / Ambient temperature

6: 25 percent / 80percent aq. AcOH / 33 h / Ambient temperature

With ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;
DOI:10.1021/jo00261a009

Reference yield:

: 117249-39-5
(1S,6R)-6-(tert-butyldimethylsilyl)-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

: 117183-97-8
8-<(1S,2S)-3-hydroxy-1-methylenepropyl>-3-methyl-6,9-bis(p-methoxybenzyl)-3,4,8-trihydroxy-6,9-diaza-1-oxaspiro<4.5>decane-7,10-dione

Guidance literature:: Multi-step reaction with 7 steps

1: BuLi / tetrahydrofuran / -100 °C

2: 49 percent / CAN / acetonitrile / 0.42 h

3: 100 percent / PPTS / acetone / 12 h / Ambient temperature

4: 1.) NaH / 1.) DMF, 2.) 2 h

5: 90 percent / Bu₄NF / CH₂Cl₂; tetrahydrofuran / 0.5 h / 25 °C

6: 78 percent / DDQ, H₂O / CH₂Cl₂ / 2 h / Ambient temperature

7: 25 percent / 80percent aq. AcOH / 33 h / Ambient temperature

With n-butyllithium; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;
DOI:10.1021/jo00261a009