(1S)-1-(3-amino-2-cyanopyrrol-4-yl)methyl-5-O-benzyl-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

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Chemical Name:(1S)-1-(3-amino-2-cyanopyrrol-4-yl)methyl-5-O-benzyl-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol
CAS No.:577978-56-4
Molecular Formula:C₂₆H₃₄N₄O₅
Molecular Weight:482.58
Hs Code.:

Synonyms:(1S)-1-(3-amino-2-cyanopyrrol-4-yl)methyl-5-O-benzyl-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

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Chemical Property of (1S)-1-(3-amino-2-cyanopyrrol-4-yl)methyl-5-O-benzyl-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

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Technology Process of (1S)-1-(3-amino-2-cyanopyrrol-4-yl)methyl-5-O-benzyl-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

There total 9 articles about (1S)-1-(3-amino-2-cyanopyrrol-4-yl)methyl-5-O-benzyl-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol 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: 39.0%

: 6011-14-9
2-aminoacetonitrile hydrochloride

: (1S)-5-O-benzyl-N-tert-butoxycarbonyl-1-(2-cyano-3-dimethylaminoallyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

: 577978-56-4
(1S)-1-(3-amino-2-cyanopyrrol-4-yl)methyl-5-O-benzyl-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: (1S)-5-O-benzyl-N-tert-butoxycarbonyl-1-(2-cyano-3-dimethylaminoallyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol; With acetic acid; In tetrahydrofuran; at 20 ℃; for 1.5h;

2-aminoacetonitrile hydrochloride; With sodium acetate; In methanol; at 20 ℃; for 16h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; methyl chloroformate; In dichloromethane; for 16h; Heating;
DOI:10.1021/jm030145r

Reference yield:

: 153172-33-9
(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole

: 577978-56-4
(1S)-1-(3-amino-2-cyanopyrrol-4-yl)methyl-5-O-benzyl-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: Multi-step reaction with 9 steps

1.1: LDA / diethyl ether / 0.33 h / -65 °C

1.2: 65 percent / diethyl ether / -65 - 20 °C

2.1: methanol / 20 °C

3.1: tetrabutylammonium fluoride / diethyl ether; tetrahydrofuran / 14 h

4.1: 15 g / NaH / dimethylformamide / 0 - 20 °C

5.1: diisobutylaluminum hydride / toluene; tetrahydrofuran / 3 h / 0 °C

6.1: diisopropylethylamine / CH₂Cl₂ / 0 - 20 °C

7.1: 40 percent / dimethylformamide / 14 h / 80 °C

8.1: 84 percent / dimethylformamide / 72 h / 70 °C

9.1: aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

9.2: NaOAc / methanol / 16 h / 20 °C

9.3: 39 percent / DBU; ClCO₂Me / CH₂Cl₂ / 16 h / Heating

With tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm030145r

Reference yield:

: (3aS,6R,6aR)-tert-butyl 4-(2-tert-butoxy-2-oxoethyl)-6-(hydroxymethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate

: 577978-56-4
(1S)-1-(3-amino-2-cyanopyrrol-4-yl)methyl-5-O-benzyl-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 15 g / NaH / dimethylformamide / 0 - 20 °C

2.1: diisobutylaluminum hydride / toluene; tetrahydrofuran / 3 h / 0 °C

3.1: diisopropylethylamine / CH₂Cl₂ / 0 - 20 °C

4.1: 40 percent / dimethylformamide / 14 h / 80 °C

5.1: 84 percent / dimethylformamide / 72 h / 70 °C

6.1: aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

6.2: NaOAc / methanol / 16 h / 20 °C

6.3: 39 percent / DBU; ClCO₂Me / CH₂Cl₂ / 16 h / Heating

With sodium hydride; diisobutylaluminium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm030145r