Benzoic acid 3-[(3S,4S)-3,4,8-trihydroxy-6,9-bis-(4-methoxy-benzyl)-3-methyl-7,10-dioxo-1-oxa-6,9-diaza-spiro[4.5]dec-8-yl]-but-3-enyl ester

Base Information

Chemical Name:Benzoic acid 3-[(3S,4S)-3,4,8-trihydroxy-6,9-bis-(4-methoxy-benzyl)-3-methyl-7,10-dioxo-1-oxa-6,9-diaza-spiro[4.5]dec-8-yl]-but-3-enyl ester
CAS No.:117183-98-9
Molecular Formula:C₃₅H₃₈N₂O₁₀
Molecular Weight:646.694
Hs Code.:

Synonyms:Benzoic acid 3-[(3S,4S)-3,4,8-trihydroxy-6,9-bis-(4-methoxy-benzyl)-3-methyl-7,10-dioxo-1-oxa-6,9-diaza-spiro[4.5]dec-8-yl]-but-3-enyl ester

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Chemical Property of Benzoic acid 3-[(3S,4S)-3,4,8-trihydroxy-6,9-bis-(4-methoxy-benzyl)-3-methyl-7,10-dioxo-1-oxa-6,9-diaza-spiro[4.5]dec-8-yl]-but-3-enyl ester

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Technology Process of Benzoic acid 3-[(3S,4S)-3,4,8-trihydroxy-6,9-bis-(4-methoxy-benzyl)-3-methyl-7,10-dioxo-1-oxa-6,9-diaza-spiro[4.5]dec-8-yl]-but-3-enyl ester

There total 8 articles about Benzoic acid 3-[(3S,4S)-3,4,8-trihydroxy-6,9-bis-(4-methoxy-benzyl)-3-methyl-7,10-dioxo-1-oxa-6,9-diaza-spiro[4.5]dec-8-yl]-but-3-enyl 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: 51.0%

: 98-88-4
benzoyl chloride

: 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

: 117183-98-9
Benzoic acid 3-[(3S,4S)-3,4,8-trihydroxy-6,9-bis-(4-methoxy-benzyl)-3-methyl-7,10-dioxo-1-oxa-6,9-diaza-spiro[4.5]dec-8-yl]-but-3-enyl ester

Guidance literature:: With pyridine; In 1,2-dichloro-ethane;
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

: 117183-98-9
Benzoic acid 3-[(3S,4S)-3,4,8-trihydroxy-6,9-bis-(4-methoxy-benzyl)-3-methyl-7,10-dioxo-1-oxa-6,9-diaza-spiro[4.5]dec-8-yl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 7 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

7: 51 percent / pyridine / 1,2-dichloro-ethane

With pyridine; 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; 1,2-dichloro-ethane; 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

: 117183-98-9
Benzoic acid 3-[(3S,4S)-3,4,8-trihydroxy-6,9-bis-(4-methoxy-benzyl)-3-methyl-7,10-dioxo-1-oxa-6,9-diaza-spiro[4.5]dec-8-yl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 8 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

8: 51 percent / pyridine / 1,2-dichloro-ethane

With pyridine; 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; 1,2-dichloro-ethane; acetone; acetonitrile;
DOI:10.1021/jo00261a009