1,2-Pyrrolidinedicarboxylic acid, 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-5-[(2Z)-4-methoxy-4- oxo-3-[[(phenylmethoxy)carbonyl]amino]-2-butenyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,5R)-

Base Information

Chemical Name:1,2-Pyrrolidinedicarboxylic acid, 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-5-[(2Z)-4-methoxy-4- oxo-3-[[(phenylmethoxy)carbonyl]amino]-2-butenyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,5R)-
CAS No.:600155-27-9
Molecular Formula:C34H39N3O10
Molecular Weight:649.698
Hs Code.:

1,2-Pyrrolidinedicarboxylic acid,
3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-5-[(2Z)-4-methoxy-4-
oxo-3-[[(phenylmethoxy)carbonyl]amino]-2-butenyl]-,
1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,5R)-

Synonyms:

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Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-5-[(2Z)-4-methoxy-4- oxo-3-[[(phenylmethoxy)carbonyl]amino]-2-butenyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,5R)-

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Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-5-[(2Z)-4-methoxy-4- oxo-3-[[(phenylmethoxy)carbonyl]amino]-2-butenyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,5R)-

There total 7 articles about 1,2-Pyrrolidinedicarboxylic acid, 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-5-[(2Z)-4-methoxy-4- oxo-3-[[(phenylmethoxy)carbonyl]amino]-2-butenyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,3S,5R)- 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:

: 100945-15-1,88568-95-0
N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

: (2S,3S,5R)-3-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-5-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 600155-27-9
methyl (2S,3S,5R)-1-(tert-butyloxycarbonyl)-3-[2-(N-phthalimido)ethyl]-5-[(3-amino-(N-benzyloxycarbonyl)-3-methoxycarbonyl)-2-propenyl]prolinate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃;
DOI:10.1021/ol0351347

Reference yield:

: (2S,3S)-3-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

: 600155-27-9
methyl (2S,3S,5R)-1-(tert-butyloxycarbonyl)-3-[2-(N-phthalimido)ethyl]-5-[(3-amino-(N-benzyloxycarbonyl)-3-methoxycarbonyl)-2-propenyl]prolinate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.77 g / DMAP / acetonitrile / 5 h

2: DIBAL-H / tetrahydrofuran; hexane / 0.25 h / -78 °C

3: p-TsOH / 3 h

4: 150 mg / BF₃*Et₂O / diethyl ether / -40 °C

5: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 4 h / 20 °C

6: 117 mg / DBU / CH₂Cl₂ / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; boron trifluoride diethyl etherate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetonitrile; 6: Horner-Emmons olefination;
DOI:10.1021/ol0351347

Reference yield:

: (2S,3S)-3-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-5-oxo-pyrrolidine-2-carboxylic acid

: 600155-27-9
methyl (2S,3S,5R)-1-(tert-butyloxycarbonyl)-3-[2-(N-phthalimido)ethyl]-5-[(3-amino-(N-benzyloxycarbonyl)-3-methoxycarbonyl)-2-propenyl]prolinate

Guidance literature:: Multi-step reaction with 7 steps

1: SOCl₂ / 0 - 20 °C

2: 1.77 g / DMAP / acetonitrile / 5 h

3: DIBAL-H / tetrahydrofuran; hexane / 0.25 h / -78 °C

4: p-TsOH / 3 h

5: 150 mg / BF₃*Et₂O / diethyl ether / -40 °C

6: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 4 h / 20 °C

7: 117 mg / DBU / CH₂Cl₂ / 20 °C

With dmap; sodium periodate; osmium(VIII) oxide; thionyl chloride; boron trifluoride diethyl etherate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetonitrile; 7: Horner-Emmons olefination;
DOI:10.1021/ol0351347