tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate
CAS No.:1393105-90-2
Molecular Formula:C₁₈H₂₇NO₆
Molecular Weight:353.415
Hs Code.:

Synonyms:tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

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Chemical Property of tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

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Technology Process of tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

There total 16 articles about tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate 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: 96.0%

: 1393105-96-8
tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

: 1393105-90-2
tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

Guidance literature:: tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate; With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Cooling with ice;

With water;
DOI:10.1002/ejoc.201200377

Reference yield:

: 1393105-88-8
tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

: 1393105-90-2
tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

: 1393105-92-4
tert-butyl (2S,3R,4S,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

Guidance literature:: With potassium osmate(VI) dihydrate; water; In acetone; at 20 ℃; for 48h; Inert atmosphere;
DOI:10.1002/ejoc.201200377

Reference yield:

: 1241959-30-7
(R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

: 1393105-90-2
tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: triethylamine / tetrahydrofuran / 20 h / 50 °C / Inert atmosphere

2: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux; Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C / Cooling with ice

4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 12 h / -75 °C / Inert atmosphere

5: water; sodium hydroxide / methanol / 3 h / 0 - 20 °C / Inert atmosphere

6: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

7: potassium osmate(VI) dihydrate; water; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / -10 °C / Inert atmosphere

8: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / Cooling with ice

With 1H-imidazole; Grubbs catalyst first generation; potassium osmate(VI) dihydrate; tetrabutyl ammonium fluoride; water; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4: Mitsunobu reaction;
DOI:10.1002/ejoc.201200377