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

Base Information

Chemical Name:(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-3-hydroxymethyl-hexahydro-indolizin-5-one
CAS No.:181705-77-1
Molecular Formula:C₁₆H₂₀N₄O₃
Molecular Weight:316.36
Hs Code.:

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

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Chemical Property of (3S,6S,8R,8aR)-6-Azido-8-benzyloxy-3-hydroxymethyl-hexahydro-indolizin-5-one

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Technology Process of (3S,6S,8R,8aR)-6-Azido-8-benzyloxy-3-hydroxymethyl-hexahydro-indolizin-5-one

There total 10 articles about (3S,6S,8R,8aR)-6-Azido-8-benzyloxy-3-hydroxymethyl-hexahydro-indolizin-5-one 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: 91.0%

: 181705-76-0
(3S,6S,8R,8aR)-6-Azido-8-benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-hexahydro-indolizin-5-one

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

Guidance literature:: With pyridine hydrogenfluoride; In acetonitrile; for 5h;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

: 100-39-0
benzyl bromide

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

Guidance literature:: Multi-step reaction with 4 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

With 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; acetonitrile;
DOI:10.1016/S0960-894X(96)00275-2

Reference yield:

: 181705-75-9
(3S,6R,8R,8aR)-8-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-hexahydro-indolizin-5-one

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

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / PPh₃, DEAD, (PhO)2P(O)N₃

2: 91 percent / HF*py / acetonitrile / 5 h

With diphenyl phosphoryl azide; pyridine hydrogenfluoride; triphenylphosphine; diethylazodicarboxylate; In acetonitrile;
DOI:10.1016/S0960-894X(96)00275-2