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

Base Information

Chemical Name:(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid 2-trimethylsilanyl-ethyl ester
CAS No.:181705-78-2
Molecular Formula:C₂₁H₃₀N₄O₄Si
Molecular Weight:430.579
Hs Code.:

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

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Chemical Property of (3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of (3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid 2-trimethylsilanyl-ethyl ester

There total 12 articles about (3S,6S,8R,8aR)-6-Azido-8-benzyloxy-5-oxo-octahydro-indolizine-3-carboxylic acid 2-trimethylsilanyl-ethyl 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: 77.0%

: 2916-68-9
2-(Trimethylsilyl)ethanol

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

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

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

: 100-39-0
benzyl bromide

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

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

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

2: 77 percent / EDCl, DMAP / acetonitrile

With dmap; jones reagent; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetone; acetonitrile;
DOI:10.1016/S0960-894X(96)00275-2