(3S,4R,5R)-5-O-benzyl-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine

Base Information

Chemical Name:(3S,4R,5R)-5-O-benzyl-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine
CAS No.:1294499-39-0
Molecular Formula:C₂₀H₂₉NO₅
Molecular Weight:363.454
Hs Code.:

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

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

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

There total 6 articles about (3S,4R,5R)-5-O-benzyl-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine 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: 75.0%

: 100-39-0
benzyl bromide

: 176485-27-1
(3S,4R,5R)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine

: 1294499-39-0
(3S,4R,5R)-5-O-benzyl-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine

Guidance literature:: With sodium hydride; In tetrahydrofuran; for 5h; Reflux;
DOI:10.1002/ejoc.201001610

Reference yield:

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

: 1294499-39-0
(3S,4R,5R)-5-O-benzyl-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine

Guidance literature:: Multi-step reaction with 3 steps

1: palladium on carbon; hydrogen / ethanol

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

3: sodium hydride / tetrahydrofuran / 5 h / Reflux

With palladium on carbon; hydrogen; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; ethanol; water;
DOI:10.1002/ejoc.201001610

Reference yield:

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

: 1294499-39-0
(3S,4R,5R)-5-O-benzyl-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine

Guidance literature:: Multi-step reaction with 5 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: sodium hydride / tetrahydrofuran / 5 h / Reflux

With pyridine; sodium azide; palladium on carbon; hydrogen; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201001610