(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-hydroxymethyl-3,4-O-isopropyliden-5-methylpyrrolidine-3,4-diol

Base Information

Chemical Name:(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-hydroxymethyl-3,4-O-isopropyliden-5-methylpyrrolidine-3,4-diol
CAS No.:1618698-49-9
Molecular Formula:C₁₇H₂₃NO₅
Molecular Weight:321.373
Hs Code.:

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

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

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

There total 5 articles about (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-hydroxymethyl-3,4-O-isopropyliden-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: 85.0%

: 869857-92-1
(2S,3S,4R,5S)-1-benzyloxycarbonyl-2-formyl-5-methylpyrrolidine-3,4-diol

: 1618698-49-9
(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-hydroxymethyl-3,4-O-isopropyliden-5-methylpyrrolidine-3,4-diol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.333333h;
DOI:10.3998/ark.5550190.p008.492

Reference yield: 85.0%

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

: 501-53-1,94274-21-2
benzyl chloroformate

: 1618698-49-9
(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-hydroxymethyl-3,4-O-isopropyliden-5-methylpyrrolidine-3,4-diol

Guidance literature:: With sodium hydrogencarbonate; In ethanol; water; at 20 ℃; for 2h;
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

: 1618698-49-9
(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-hydroxymethyl-3,4-O-isopropyliden-5-methylpyrrolidine-3,4-diol

Guidance literature:: Multi-step reaction with 6 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

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