(3S,4R,5R)-5-(benzylamino)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxypiperidine

Base Information

Chemical Name:(3S,4R,5R)-5-(benzylamino)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxypiperidine
CAS No.:1294499-35-6
Molecular Formula:C₂₀H₃₀N₂O₄
Molecular Weight:362.469
Hs Code.:

Synonyms:(3S,4R,5R)-5-(benzylamino)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxypiperidine

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Chemical Property of (3S,4R,5R)-5-(benzylamino)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxypiperidine

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Technology Process of (3S,4R,5R)-5-(benzylamino)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxypiperidine

There total 7 articles about (3S,4R,5R)-5-(benzylamino)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxypiperidine 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: 64.0%

: 100-46-9
benzylamine

: 176245-04-8
(4S,5S)-1-(tert-butoxycarbonyl)-4,5-O-isopropylidene-4,5-dihydroxypiperidin-3-one

: 1294499-35-6
(3S,4R,5R)-5-(benzylamino)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxypiperidine

Guidance literature:: With sodium triacetoxyborohydride; In dichloromethane; at 20 ℃; for 5h; Inert atmosphere;
DOI:10.1002/ejoc.201001610

Reference yield:

: 98391-41-4
benzyl 5-azido-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside

: 1294499-35-6
(3S,4R,5R)-5-(benzylamino)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxypiperidine

Guidance literature:: Multi-step reaction with 4 steps

1: palladium on carbon; hydrogen / ethanol

2: sodium hydrogencarbonate / ethanol; water / 1 h / 20 °C

3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

4: sodium triacetoxyborohydride / dichloromethane / 5 h / 20 °C / Inert atmosphere

With sodium triacetoxyborohydride; palladium on carbon; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; In ethanol; dichloromethane; water;
DOI:10.1002/ejoc.201001610

Reference yield:

: 23276-32-6
benzyl 2,3-O-isopropylidene-D-ribofuranoside

: 1294499-35-6
(3S,4R,5R)-5-(benzylamino)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxypiperidine

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / 720 h / 20 °C

2: sodium azide / N,N-dimethyl-formamide / 80 °C

3: palladium on carbon; hydrogen / ethanol

4: sodium hydrogencarbonate / ethanol; water / 1 h / 20 °C

5: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

6: sodium triacetoxyborohydride / dichloromethane / 5 h / 20 °C / Inert atmosphere

With pyridine; sodium azide; sodium triacetoxyborohydride; palladium on carbon; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201001610