[1-Amino-1-(4-{[((3S,6S,8S,8aS)-6-benzyl-6-hydroxy-8-methoxy-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,8S,8aS)-6-benzyl-6-hydroxy-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester
CAS No.:267661-38-1
Molecular Formula:C₃₃H₃₆N₄O₆
Molecular Weight:584.672
Hs Code.:

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

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

Chemical Property:

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

There total 12 articles about [1-Amino-1-(4-{[((3S,6S,8S,8aS)-6-benzyl-6-hydroxy-8-methoxy-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:

: 181705-70-4
(5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone

: 267661-38-1
[1-Amino-1-(4-{[((3S,6S,8S,8aS)-6-benzyl-6-hydroxy-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 96 percent / H₂ / 10 percent Pd/C / ethyl acetate

2: 71 percent / B-bromocatecholborane / CH₂Cl₂

3: 98 percent / NaOMe / methanol

4: 86 percent / Ag₂O / acetonitrile

5: t-BuLi / tetrahydrofuran / -78 °C

6: t-BuLi; Davis achiral oxaziridine / tetrahydrofuran / -78 °C

7: Pyr; DMAP

8: TBAF / tetrahydrofuran

9: TPAP; NMP / CH₂Cl₂

10: t-BuOH; NaClO₄; NaH₂PO₄ / H₂O

11: BOP; i-Pr₂EtN / CH₂Cl₂

12: MeONa / methanol

With pyridine; 1-methyl-pyrrolidin-2-one; dmap; sodium dihydrogenphosphate; tetrapropylammonium perruthennate; Davis achiral oxaziridine; bromocatecholborane; sodium perchlorate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium methylate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; silver(l) oxide; tert-butyl alcohol; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile; 1: Catalytic hydrogenation / 2: Decarboxylation / 3: lactam formation / 4: Etherification / 5: Alkylation / 6: Rearrangement / 7: Acetylation / 8: desilylation / 9: Oxidation / 10: Oxidation / 11: Acylation / 12: Deacetylation;
DOI:10.1016/S0960-894X(99)00669-1

Reference yield:

: 267661-37-0
Acetic acid (3S,6S,8S,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-8-methoxy-5-oxo-octahydro-indolizin-6-yl ester

: 267661-38-1
[1-Amino-1-(4-{[((3S,6S,8S,8aS)-6-benzyl-6-hydroxy-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester

Guidance literature:: With sodium methylate; In methanol;
DOI:10.1016/S0960-894X(99)00669-1

Reference yield:

: 181705-71-5
(5S,2'S,5'S)-5-[5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'yl]-tetrahydrofuran-2-one

: 267661-38-1
[1-Amino-1-(4-{[((3S,6S,8S,8aS)-6-benzyl-6-hydroxy-8-methoxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / NaOMe / methanol

2: 86 percent / Ag₂O / acetonitrile

3: t-BuLi / tetrahydrofuran / -78 °C

4: t-BuLi; Davis achiral oxaziridine / tetrahydrofuran / -78 °C

5: Pyr; DMAP

6: TBAF / tetrahydrofuran

7: TPAP; NMP / CH₂Cl₂

8: t-BuOH; NaClO₄; NaH₂PO₄ / H₂O

9: BOP; i-Pr₂EtN / CH₂Cl₂

10: MeONa / methanol

With pyridine; 1-methyl-pyrrolidin-2-one; dmap; sodium dihydrogenphosphate; tetrapropylammonium perruthennate; Davis achiral oxaziridine; sodium perchlorate; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium methylate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; silver(l) oxide; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1: lactam formation / 2: Etherification / 3: Alkylation / 4: Rearrangement / 5: Acetylation / 6: desilylation / 7: Oxidation / 8: Oxidation / 9: Acylation / 10: Deacetylation;
DOI:10.1016/S0960-894X(99)00669-1