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

Base Information

• Chemical Name: Acetic acid (3S,6R,8aS)-6-benzyl-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester
• CAS No.: 267661-31-4
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.385

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

Chemical Property of Acetic acid (3S,6R,8aS)-6-benzyl-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (3S,6R,8aS)-6-benzyl-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester

There total 10 articles about Acetic acid (3S,6R,8aS)-6-benzyl-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl 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: 60.0%

Acetic acid (3S,6R,8aS)-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-octahydro-indolizin-6-yl ester (267661-13-2) → Acetic acid (3S,6R,8aS)-6-benzyl-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester (267661-31-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

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) → Acetic acid (3S,6R,8aS)-6-benzyl-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester (267661-31-4)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; carbon disulfide; dmap; 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; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 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;

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) → Acetic acid (3S,6R,8aS)-6-benzyl-3-hydroxymethyl-5-oxo-octahydro-indolizin-6-yl ester (267661-31-4)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; carbon disulfide; dmap; 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; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; 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;

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

upstream raw materials:

Acetic acid (3S,6R,8aS)-6-benzyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-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

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

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

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