(3S,6R,8aS)-6-Acetoxy-6-benzyl-5-oxo-octahydro-indolizine-3-carboxylic acid

Base Information

• Chemical Name: (3S,6R,8aS)-6-Acetoxy-6-benzyl-5-oxo-octahydro-indolizine-3-carboxylic acid
• CAS No.: 267661-14-3
• Molecular Formula: C₁₈H₂₁NO₅
• Molecular Weight: 331.368

Synonyms:(3S,6R,8aS)-6-Acetoxy-6-benzyl-5-oxo-octahydro-indolizine-3-carboxylic acid

Chemical Property of (3S,6R,8aS)-6-Acetoxy-6-benzyl-5-oxo-octahydro-indolizine-3-carboxylic acid

Chemical Property:

Purity/Quality:

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Technology Process of (3S,6R,8aS)-6-Acetoxy-6-benzyl-5-oxo-octahydro-indolizine-3-carboxylic acid

There total 12 articles about (3S,6R,8aS)-6-Acetoxy-6-benzyl-5-oxo-octahydro-indolizine-3-carboxylic acid 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: 100.0%

Acetic acid (3S,6R,8aS)-6-benzyl-3-formyl-5-oxo-octahydro-indolizin-6-yl ester (267661-32-5) → (3S,6R,8aS)-6-Acetoxy-6-benzyl-5-oxo-octahydro-indolizine-3-carboxylic acid (267661-14-3)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; tert-butyl alcohol; In water;

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) → (3S,6R,8aS)-6-Acetoxy-6-benzyl-5-oxo-octahydro-indolizine-3-carboxylic acid (267661-14-3)

Guidance literature:

Multi-step reaction with 12 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: 88 percent / t-BuLi / tetrahydrofuran / -78 °C

6.1: 63 percent / t-BuLi; Davis' achiral oxaziridine / tetrahydrofuran / -78 °C

7.1: 79 percent / DDQ / CH₂Cl₂; ethyl acetate

8.1: NaH, CS₂, MeI / tetrahydrofuran

8.2: 48 percent / Ph₃SnH; AIBN / toluene / 0.5 h / Heating

9.1: 82 percent / Pyr; DMAP

10.1: 60 percent / TBAF / tetrahydrofuran

11.1: 60 percent / TPAP; NMO / CH₂Cl₂

12.1: 100 percent / t-BuOH; NaClO₂; NaH₂PO₄ / H₂O

With pyridine; carbon disulfide; dmap; sodium chlorite; sodium dihydrogenphosphate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; Davis' achiral oxaziridine; bromocatecholborane; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; 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: Alkylation / 6.1: Rearrangement / 7.1: cleavage / 8.1: deoxygenation / 8.2: Reduction / 9.1: Acetylation / 10.1: desilylation / 11.1: Oxidation / 12.1: Oxidation;

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) → (3S,6R,8aS)-6-Acetoxy-6-benzyl-5-oxo-octahydro-indolizine-3-carboxylic acid (267661-14-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 98 percent / NaOMe / methanol

2.1: 86 percent / Bu₄NI / tetrahydrofuran

3.1: 88 percent / t-BuLi / tetrahydrofuran / -78 °C

4.1: 63 percent / t-BuLi; Davis' achiral oxaziridine / tetrahydrofuran / -78 °C

5.1: 79 percent / DDQ / CH₂Cl₂; ethyl acetate

6.1: NaH, CS₂, MeI / tetrahydrofuran

6.2: 48 percent / Ph₃SnH; AIBN / toluene / 0.5 h / Heating

7.1: 82 percent / Pyr; DMAP

8.1: 60 percent / TBAF / tetrahydrofuran

9.1: 60 percent / TPAP; NMO / CH₂Cl₂

10.1: 100 percent / t-BuOH; NaClO₂; NaH₂PO₄ / H₂O

With pyridine; carbon disulfide; dmap; sodium chlorite; sodium dihydrogenphosphate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; Davis' achiral oxaziridine; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 1.1: lactam formation / 2.1: Etherification / 3.1: Alkylation / 4.1: Rearrangement / 5.1: cleavage / 6.1: deoxygenation / 6.2: Reduction / 7.1: Acetylation / 8.1: desilylation / 9.1: Oxidation / 10.1: Oxidation;

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

upstream raw materials:

Acetic acid (3S,6R,8aS)-6-benzyl-3-formyl-5-oxo-octahydro-indolizin-6-yl ester

(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

Downstream raw materials:

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

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

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