(3S,6S,8R,8aR)-8-Benzyloxy-6-(2-1H-indol-3-yl-acetylamino)-5-oxo-octahydro-indolizine-3-carboxylic acid

Base Information

Chemical Name:(3S,6S,8R,8aR)-8-Benzyloxy-6-(2-1H-indol-3-yl-acetylamino)-5-oxo-octahydro-indolizine-3-carboxylic acid
CAS No.:849364-86-9
Molecular Formula:C₂₆H₂₇N₃O₅
Molecular Weight:461.517
Hs Code.:

Synonyms:(3S,6S,8R,8aR)-8-Benzyloxy-6-(2-1H-indol-3-yl-acetylamino)-5-oxo-octahydro-indolizine-3-carboxylic acid

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Chemical Property of (3S,6S,8R,8aR)-8-Benzyloxy-6-(2-1H-indol-3-yl-acetylamino)-5-oxo-octahydro-indolizine-3-carboxylic acid

Chemical Property:

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Technology Process of (3S,6S,8R,8aR)-8-Benzyloxy-6-(2-1H-indol-3-yl-acetylamino)-5-oxo-octahydro-indolizine-3-carboxylic acid

There total 10 articles about (3S,6S,8R,8aR)-8-Benzyloxy-6-(2-1H-indol-3-yl-acetylamino)-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:

: 181705-79-3
(3S,6S,8R,8aR)-8-Benzyloxy-6-(2-1H-indol-3-yl-acetylamino)-5-oxo-octahydro-indolizine-3-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 849364-86-9
(3S,6S,8R,8aR)-8-Benzyloxy-6-(2-1H-indol-3-yl-acetylamino)-5-oxo-octahydro-indolizine-3-carboxylic acid

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

: 100-39-0
benzyl bromide

: 849364-86-9
(3S,6S,8R,8aR)-8-Benzyloxy-6-(2-1H-indol-3-yl-acetylamino)-5-oxo-octahydro-indolizine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / NaH, TBAI / tetrahydrofuran / 18 h

2: 81 percent / t-BuLi, O₂, (MeO)3P, NH₄Cl / tetrahydrofuran / 0.3 h / -78 °C

3: 76 percent / PPh₃, DEAD, (PhO)2P(O)N₃

4: 91 percent / HF*py / acetonitrile / 5 h

5: 86 percent / Jones reagent / acetone / 1 h / 0 °C

6: 77 percent / EDCl, DMAP / acetonitrile

7: H₂, NH₄OAc / Pd/C / 0.08 h / 760 Torr

8: BOP / acetonitrile / 1 h / 0 °C

9: TBAF / tetrahydrofuran / 1 h / 0 °C

With dmap; jones reagent; diphenyl phosphoryl azide; ammonium acetate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; oxygen; tetra-(n-butyl)ammonium iodide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ammonium chloride; pyridine hydrogenfluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; diethylazodicarboxylate; phosphorous acid trimethyl ester; palladium on activated charcoal; In tetrahydrofuran; acetone; acetonitrile;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

: 181705-78-2
(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 849364-86-9
(3S,6S,8R,8aR)-8-Benzyloxy-6-(2-1H-indol-3-yl-acetylamino)-5-oxo-octahydro-indolizine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: H₂, NH₄OAc / Pd/C / 0.08 h / 760 Torr

2: BOP / acetonitrile / 1 h / 0 °C

3: TBAF / tetrahydrofuran / 1 h / 0 °C

With ammonium acetate; tetrabutyl ammonium fluoride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; acetonitrile;
DOI:10.1016/S0960-894X(96)00275-2