(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid

Base Information

Chemical Name:(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid
CAS No.:181705-69-1
Molecular Formula:C₁₆H₁₈N₄O₄
Molecular Weight:330.343
Hs Code.:

Synonyms:(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid

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Chemical Property of (3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid

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Technology Process of (3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid

There total 12 articles about (3S,6S,8R,8aR)-6-Azido-8-benzyloxy-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: 94.0%

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

: 181705-69-1
(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-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: 86.0%

: 181705-77-1
(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-3-hydroxymethyl-hexahydro-indolizin-5-one

: 181705-69-1
(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid

Guidance literature:: With jones reagent; In acetone; at 0 ℃; for 1h;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

: 100-39-0
benzyl bromide

: 181705-69-1
(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 5 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

With jones reagent; diphenyl phosphoryl azide; tert.-butyl lithium; oxygen; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; pyridine hydrogenfluoride; triphenylphosphine; diethylazodicarboxylate; phosphorous acid trimethyl ester; In tetrahydrofuran; acetone; acetonitrile;
DOI:10.1016/S0960-894X(96)00275-2