(2S,3S,4R,5S)-2-[1-((4-benzyloxycarbonyl-5-methylfuran-2-yl)-methyl)-1H-1,2,3-triazol-4-yl]-5-methylpyrrolidine-3,4-diol

Base Information

Chemical Name:(2S,3S,4R,5S)-2-[1-((4-benzyloxycarbonyl-5-methylfuran-2-yl)-methyl)-1H-1,2,3-triazol-4-yl]-5-methylpyrrolidine-3,4-diol
CAS No.:1618698-75-1
Molecular Formula:C₂₁H₂₄N₄O₅
Molecular Weight:412.445
Hs Code.:

Synonyms:(2S,3S,4R,5S)-2-[1-((4-benzyloxycarbonyl-5-methylfuran-2-yl)-methyl)-1H-1,2,3-triazol-4-yl]-5-methylpyrrolidine-3,4-diol

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Chemical Property of (2S,3S,4R,5S)-2-[1-((4-benzyloxycarbonyl-5-methylfuran-2-yl)-methyl)-1H-1,2,3-triazol-4-yl]-5-methylpyrrolidine-3,4-diol

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Technology Process of (2S,3S,4R,5S)-2-[1-((4-benzyloxycarbonyl-5-methylfuran-2-yl)-methyl)-1H-1,2,3-triazol-4-yl]-5-methylpyrrolidine-3,4-diol

There total 12 articles about (2S,3S,4R,5S)-2-[1-((4-benzyloxycarbonyl-5-methylfuran-2-yl)-methyl)-1H-1,2,3-triazol-4-yl]-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: 54.0%

: 1618698-55-7
(2S,3S,4R,5S)-2-ethynyl-5-methylpyrrolidine-3,4-diol

: 1618698-60-4
benzyl 5-(azidomethyl)-2-methylfuran-3-carboxylate

: 1618698-75-1
(2S,3S,4R,5S)-2-[1-((4-benzyloxycarbonyl-5-methylfuran-2-yl)-methyl)-1H-1,2,3-triazol-4-yl]-5-methylpyrrolidine-3,4-diol

Guidance literature:: With copper(II) sulfate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20 ℃; for 24h;
DOI:10.1039/c4ob00931b

Reference yield:

: 1334598-36-5
C₁₄H₁₂O₄

: 1618698-75-1
(2S,3S,4R,5S)-2-[1-((4-benzyloxycarbonyl-5-methylfuran-2-yl)-methyl)-1H-1,2,3-triazol-4-yl]-5-methylpyrrolidine-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1: sodium tetrahydroborate / 0.5 h

2: N-chloro-succinimide; dimethylsulfide / dichloromethane / 1 h / -20 - 5 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 0.17 h / 20 °C

4: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C

With sodium tetrahydroborate; N-chloro-succinimide; sodium azide; dimethylsulfide; copper(II) sulfate; sodium L-ascorbate; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1039/c4ob00931b

Reference yield:

: 1618698-50-2
(2S,3S,4R,5S)-N-tert-butoxycarbonyl-2-hydroxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

: 1618698-75-1
(2S,3S,4R,5S)-2-[1-((4-benzyloxycarbonyl-5-methylfuran-2-yl)-methyl)-1H-1,2,3-triazol-4-yl]-5-methylpyrrolidine-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

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

2: potassium carbonate; dimethyl 1-(1-diazo-2-oxopropyl)phosphonate / methanol / 7 h / 0 - 20 °C

3: trifluoroacetic acid / water / 2.5 h / 20 °C

4: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 24 h / 20 °C

With dimethyl 1-(1-diazo-2-oxopropyl)phosphonate; potassium carbonate; Dess-Martin periodane; copper(II) sulfate; sodium L-ascorbate; trifluoroacetic acid; In methanol; dichloromethane; water; tert-butyl alcohol; 1: |Dess-Martin Oxidation;
DOI:10.1039/c4ob00931b