(2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-benzyl-5-(benzyloxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol

Base Information

Chemical Name:(2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-benzyl-5-(benzyloxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol
CAS No.:1155985-97-9
Molecular Formula:C₂₅H₃₂N₂O₃
Molecular Weight:408.541
Hs Code.:

Synonyms:(2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-benzyl-5-(benzyloxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol

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Chemical Property of (2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-benzyl-5-(benzyloxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol

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Technology Process of (2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-benzyl-5-(benzyloxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol

There total 4 articles about (2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-benzyl-5-(benzyloxymethyl)-3,4-O-isopropylidenepyrrolidine-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: 57.0%

: 1155985-83-3
(2R,3S,4R,5S)-1-benzyl-5-(benzyloxymethyl)-2-cyano-3,4-O-isopropylidenepyrrolidine-3,4-diol

: 925-90-6
ethylmagnesium bromide

: 1155985-97-9
(2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-benzyl-5-(benzyloxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol

Guidance literature:: (2R,3S,4R,5S)-1-benzyl-5-(benzyloxymethyl)-2-cyano-3,4-O-isopropylidenepyrrolidine-3,4-diol; ethylmagnesium bromide; With methyltriisopropoxytitanium(IV); In tetrahydrofuran; diethyl ether; at 20 ℃; for 1h;

With boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; at 20 ℃; for 1h;
DOI:10.1016/j.tetlet.2009.02.135

Reference yield:

: (1R)-5-O-benzyl-1-(benzylamino)-1-cyano-1-deoxy-2,3-O-isopropylidene-D-ribose

: 1155985-97-9
(2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-benzyl-5-(benzyloxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridine; methanesulfonyl chloride / 1 h / 80 °C

2.1: methyltriisopropoxytitanium(IV) / tetrahydrofuran; diethyl ether / 1 h / 20 °C

2.2: 1 h / 20 °C

With pyridine; methyltriisopropoxytitanium(IV); methanesulfonyl chloride; In tetrahydrofuran; diethyl ether; 2.1: Kulinkovich reaction / 2.2: Kulinkovich reaction;
DOI:10.1016/j.tet.2011.12.024

Reference yield:

: 198969-39-0
5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose

: 1155985-97-9
(2R,3S,4R,5S)-2-(1-aminocyclopropyl)-1-benzyl-5-(benzyloxymethyl)-3,4-O-isopropylidenepyrrolidine-3,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: titanium(IV) isopropylate / methanol / 24 h / 20 °C

2.1: pyridine; methanesulfonyl chloride / 1 h / 80 °C

3.1: methyltriisopropoxytitanium(IV) / tetrahydrofuran; diethyl ether / 1 h / 20 °C

3.2: 1 h / 20 °C

With pyridine; titanium(IV) isopropylate; methyltriisopropoxytitanium(IV); methanesulfonyl chloride; In tetrahydrofuran; methanol; diethyl ether; 3.1: Kulinkovich reaction / 3.2: Kulinkovich reaction;
DOI:10.1016/j.tet.2011.12.024