(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Base Information

Chemical Name:(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol
CAS No.:1618698-52-4
Molecular Formula:C₁₇H₂₂N₄O₄
Molecular Weight:346.386
Hs Code.:

Synonyms:(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

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Chemical Property of (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

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Technology Process of (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

There total 7 articles about (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol 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:

: 1632124-94-7
(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-tosyloxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

: 1618698-52-4
(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 70 ℃; for 3h;
DOI:10.3998/ark.5550190.p008.492

Reference yield:

: 1618698-48-8
(2S,3S,4R,5S)-2-hydroxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

: 1618698-52-4
(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Guidance literature:: Multi-step reaction with 3 steps

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

2: pyridine / 0 - 20 °C

3: sodium azide / N,N-dimethyl-formamide / 2 h / 70 °C

With pyridine; sodium azide; sodium hydrogencarbonate; In ethanol; water; N,N-dimethyl-formamide;
DOI:10.1039/c4ob00931b

Reference yield:

: (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

: 1618698-52-4
(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Guidance literature:: Multi-step reaction with 8 steps

1: sodium hydrogencarbonate; hydroxylamine hydrochloride / ethanol; water / 72 h / 20 °C

2: pyridine / water / 6 h / 0 - 20 °C

3: toluene / 7 h / 70 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

5: hydrogen; palladium 10% on activated carbon / methanol / 24 h / 10343.2 Torr

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

7: pyridine / 0 - 20 °C

8: sodium azide / N,N-dimethyl-formamide / 2 h / 70 °C

With pyridine; sodium azide; palladium 10% on activated carbon; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;
DOI:10.1039/c4ob00931b