(1S,2R,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate

Base Information

Chemical Name:(1S,2R,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate
CAS No.:1395821-14-3
Molecular Formula:C₂₈H₃₇NO₅Si
Molecular Weight:495.691
Hs Code.:

Synonyms:(1S,2R,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate

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Chemical Property of (1S,2R,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate

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Technology Process of (1S,2R,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate

There total 5 articles about (1S,2R,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate 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: 68.0%

: C₂₄H₃₃NO₃Si

: 108-24-7
acetic anhydride

: 1395819-43-8
(1R,2S,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate

: 1395821-14-3
(1S,2R,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; Inert atmosphere;
DOI:10.1021/jo3011914

Reference yield:

: 1395819-35-8
(2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)piperidin-1-ol

: 1395819-43-8
(1R,2S,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate

: 1395821-14-3
(1S,2R,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate

Guidance literature:: Multi-step reaction with 5 steps

1: hydrogen / ethyl acetate / 1.25 h / 20 °C

2: indium; hydrogenchloride / ethanol / 2 h / 80 - 100 °C / Inert atmosphere

3: bis(4-chlorobenzyl) diazene-1,2-dicarboxylate; triphenylphosphine / dichloromethane / 1.17 h / 0 °C / Inert atmosphere

4: AD-mix-α; methanesulfonamide / water; tert-butyl alcohol / 96 h / 0 - 4 °C

5: dmap; pyridine / dichloromethane / 20 °C / Inert atmosphere

With pyridine; bis(4-chlorobenzyl) diazene-1,2-dicarboxylate; hydrogenchloride; dmap; indium; methanesulfonamide; AD-mix-α; hydrogen; triphenylphosphine; In ethanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/jo3011914

Reference yield:

: 1395819-33-6
(2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-((Z)-3-hydroxyprop-1-enyl)piperidine

: 1395819-43-8
(1R,2S,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate

: 1395821-14-3
(1S,2R,8S,8aR)-8-(tert-butyldiphenylsilyloxy)octahydroindolizine-1,2-diyl diacetate

Guidance literature:: Multi-step reaction with 3 steps

1: bis(4-chlorobenzyl) diazene-1,2-dicarboxylate; triphenylphosphine / dichloromethane / 1.17 h / 0 °C / Inert atmosphere

2: AD-mix-α; methanesulfonamide / water; tert-butyl alcohol / 96 h / 0 - 4 °C

3: dmap; pyridine / dichloromethane / 20 °C / Inert atmosphere

With pyridine; bis(4-chlorobenzyl) diazene-1,2-dicarboxylate; dmap; methanesulfonamide; AD-mix-α; triphenylphosphine; In dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo3011914