[1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester

Base Information

• Chemical Name: [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester
• CAS No.: 267661-45-0
• Molecular Formula: C₂₆H₃₀N₄O₅
• Molecular Weight: 478.548

Synonyms:[1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester

Chemical Property of [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester

There total 14 articles about [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl 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: 82.0%

(3S,6S,8aS)-6-Hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carboxylic acid (267661-19-8) + benzyl amino[4-(aminomethyl)phenyl]methylenecarbamate → [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester (267661-45-0)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0960-894X(99)00669-1

Reference yield:

(5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone (181705-70-4) → [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester (267661-45-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 96 percent / H₂ / 10 percent Pd/C / ethyl acetate

2.1: 71 percent / B-bromocatecholborane / CH₂Cl₂

3.1: 98 percent / NaOMe / methanol

4.1: 86 percent / Bu₄NI / tetrahydrofuran

5.1: 97 percent / t-BuLi / tetrahydrofuran / -78 °C

6.1: 64 percent / t-BuLi; (MeO)3P; O₂ / tetrahydrofuran / -78 °C

7.1: 84 percent / DDQ / CH₂Cl₂; H₂O

8.1: NaH; CS₂; MeI / tetrahydrofuran

8.2: 67 percent / Ph₃SnH; AIBN / toluene / 0.5 h / Heating

9.1: 92 percent / Pyr; DMAP

10.1: 75 percent / TBAF / tetrahydrofuran

11.1: 84 percent / Swern reagent

12.1: 93 percent / t-BuOH; NaClO₂; NaH₂PO₄ / H₂O

13.1: 63 percent / LiOH; H₂O₂ / tetrahydrofuran

14.1: 82 percent / BOP; i-Pr₂EtN / CH₂Cl₂

With pyridine; carbon disulfide; dmap; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; swern reagent; bromocatecholborane; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; oxygen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; phosphorous acid trimethyl ester; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 1.1: Catalytic hydrogenation / 2.1: Decarboxylation / 3.1: lactam formation / 4.1: Etherification / 5.1: Methylation / 6.1: hydroxylation / 7.1: deprotection / 8.1: deoxygenation / 8.2: deoxygenation / 9.1: Acetylation / 10.1: desilylation / 11.1: Oxidation / 12.1: Oxidation / 13.1: Deacetylation / 14.1: Acylation;

DOI:10.1016/S0960-894X(99)00669-1

Reference yield:

(5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one (181705-71-5) → [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester (267661-45-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 98 percent / NaOMe / methanol

2.1: 86 percent / Bu₄NI / tetrahydrofuran

3.1: 97 percent / t-BuLi / tetrahydrofuran / -78 °C

4.1: 64 percent / t-BuLi; (MeO)3P; O₂ / tetrahydrofuran / -78 °C

5.1: 84 percent / DDQ / CH₂Cl₂; H₂O

6.1: NaH; CS₂; MeI / tetrahydrofuran

6.2: 67 percent / Ph₃SnH; AIBN / toluene / 0.5 h / Heating

7.1: 92 percent / Pyr; DMAP

8.1: 75 percent / TBAF / tetrahydrofuran

9.1: 84 percent / Swern reagent

10.1: 93 percent / t-BuOH; NaClO₂; NaH₂PO₄ / H₂O

11.1: 63 percent / LiOH; H₂O₂ / tetrahydrofuran

12.1: 82 percent / BOP; i-Pr₂EtN / CH₂Cl₂

With pyridine; carbon disulfide; dmap; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; swern reagent; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; oxygen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; phosphorous acid trimethyl ester; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: lactam formation / 2.1: Etherification / 3.1: Methylation / 4.1: hydroxylation / 5.1: deprotection / 6.1: deoxygenation / 6.2: deoxygenation / 7.1: Acetylation / 8.1: desilylation / 9.1: Oxidation / 10.1: Oxidation / 11.1: Deacetylation / 12.1: Acylation;

DOI:10.1016/S0960-894X(99)00669-1

upstream raw materials:

(3S,6S,8aS)-6-Hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carboxylic acid

(5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one

(3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one

(5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone

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