(-)-((1S,2R,3S,6S,7aR)-6-fluorohexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizin-1-yl)methyl bis(phenylmethyl) phosphate

Base Information

Chemical Name:(-)-((1S,2R,3S,6S,7aR)-6-fluorohexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizin-1-yl)methyl bis(phenylmethyl) phosphate
CAS No.:935469-03-7
Molecular Formula:C₄₀H₄₀FN₂O₅P
Molecular Weight:678.74
Hs Code.:

Synonyms:(-)-((1S,2R,3S,6S,7aR)-6-fluorohexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizin-1-yl)methyl bis(phenylmethyl) phosphate

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Chemical Property of (-)-((1S,2R,3S,6S,7aR)-6-fluorohexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizin-1-yl)methyl bis(phenylmethyl) phosphate

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Technology Process of (-)-((1S,2R,3S,6S,7aR)-6-fluorohexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizin-1-yl)methyl bis(phenylmethyl) phosphate

There total 6 articles about (-)-((1S,2R,3S,6S,7aR)-6-fluorohexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizin-1-yl)methyl bis(phenylmethyl) phosphate 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: 59.0%

: 935469-00-4
(-)-(1S,2R,3S,6S,7aR)-6-fluorohexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide

: 108549-23-1
Dibenzyl N,N-diisopropylphosphoramidite

: 935469-03-7
(-)-((1S,2R,3S,6S,7aR)-6-fluorohexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizin-1-yl)methyl bis(phenylmethyl) phosphate

Guidance literature:: (-)-(1S,2R,3S,6S,7aR)-6-fluorohexahydro-1-(hydroxymethyl)-3-(naphthalen-2-yl)-N-(phenylmethyl)-1H-pyrrolizine-2-carboxamide; Dibenzyl N,N-diisopropylphosphoramidite; With 1H-tetrazole; In acetonitrile; at 20 ℃; for 3h;

With 3-chloro-benzenecarboperoxoic acid; In acetonitrile; at 20 ℃; for 0.5h; Further stages.;
DOI:10.1002/hlca.200790028

Reference yield:

: 935468-53-4
(-)-(3aR,4S,7R,8aR,8bS)-hexahydro-7-hydroxy-4-(naphthalen-2-yl)-2-(phenylmethyl)pyrrolo[3,4-a]pyrrolizine-1,3(2H,4H)-dione

: 935469-03-7
(-)-((1S,2R,3S,6S,7aR)-6-fluorohexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizin-1-yl)methyl bis(phenylmethyl) phosphate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / DAST / CH₂Cl₂ / 3 h / -78 - 20 °C

2.1: NaOH / tetrahydrofuran; H₂O / 15 h / 20 °C

2.2: 70 percent / SOCl₂ / 15 h / 20 °C

3.1: 58 percent / DIBAL-H / tetrahydrofuran; toluene / 2 h / 0 °C

4.1: 1H-tetrazole / acetonitrile / 3 h / 20 °C

4.2: 59 percent / mCPBA / acetonitrile / 0.5 h / 20 °C

With 1H-tetrazole; sodium hydroxide; diisobutylaluminium hydride; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;
DOI:10.1002/hlca.200790028

Reference yield:

: 935468-94-3
(-)-(3aR,4S,7S,8aR,8bS)-7-fluorohexahydro-4-(naphthalen-2-yl)-2-(phenylmethyl)pyrrolo[3,4-a]pyrrolizine-1,3(2H,4H)-dione

: 935469-03-7
(-)-((1S,2R,3S,6S,7aR)-6-fluorohexahydro-3-(naphthalen-2-yl)-2-{[(phenylmethyl)amino]carbonyl}-1H-pyrrolizin-1-yl)methyl bis(phenylmethyl) phosphate

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaOH / tetrahydrofuran; H₂O / 15 h / 20 °C

1.2: 70 percent / SOCl₂ / 15 h / 20 °C

2.1: 58 percent / DIBAL-H / tetrahydrofuran; toluene / 2 h / 0 °C

3.1: 1H-tetrazole / acetonitrile / 3 h / 20 °C

3.2: 59 percent / mCPBA / acetonitrile / 0.5 h / 20 °C

With 1H-tetrazole; sodium hydroxide; diisobutylaluminium hydride; In tetrahydrofuran; water; toluene; acetonitrile;
DOI:10.1002/hlca.200790028