127221-57-2

Upstream product

• 100-39-0 benzyl bromide 
• 155727-03-0 (2R,5R)-2-Benzyloxymethyl-5-hydroxymethylpyrrolidine 
• 127221-56-1 1,6-di-O-benzyl-2,5-di-O-tosyl-3,4-dideoxy-D-threo-hexitol 
• 24211-51-6 (2S,5S)-hexane-1,2,5,6-tetrol 
• 146547-11-7 (2S,5S)-1,6-bis[(tert-butyldiphenylsilyl)oxy]hexane-2,5-diol 
• 146547-15-1 1,6-di-O-(t-butyl-diphenyl)-silyl-2,5-di-O-tosyl-3,4-dideoxy-D-threo-hexitol 
• 100-46-9 benzylamine 
• 3268-36-8 1,2:5,6-di-O-isopropylidene-3,4-O-thioxocarbonyl-D-mannitol 
• 31843-48-8 trans-3,4-Didehydro-3,4-dideoxy-1,2:5,6-di-O-isopropyliden-D-threo-hexitol 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 127305-27-5 1,2-bis<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>ethane 
• 146547-12-8 1,6-di-O-(tert-butyldiphenyl)silyl-2,5-di-O-isopropylidene-3,4-dideoxy-D-threo-hexitol 
• 146547-21-9 C₂₀H₂₆O₈S₂ 
• 146547-14-0 1,6-di-O-benzyl-2,5-di-O-isopropylidene-3,4-dideoxy-D-threo-hexitol 

Downstream Products

• 127221-54-9 trans-(2R,5R)-bis(benzyloxymethyl)-pyrrolidine 

Relevant academic research and scientific papers

Highly diastereoselective route to trans-S-substituted 2-hydroxymethylpyrrolidine derivatives by radical cyclisation

The cyclisation of radical species generated from (S)-N-(3-bromopropyl)oxazolin-2-ones 22 by treatment with tributylstannane in the presence of AIBN yielded 5-substituted pyrrolooxazolones with high diastereoselectivity. In the same reaction using (±)-N-(3-bromobutyl)oxazolin-2-one 25a or (±)-N-(4-bromopentan-2-yl)oxazolin-2-one 25b, the radical cyclisation gave predominantly the (5S*,7S*,7aR*)-5,7-disubstituted pyrrolooxazolines rather than the (5S*,7R*,7aR*) products. The radical cyclisation of 4-phenylsulfanyloxazolidinones 29a,b also resulted in the predominant formation of the corresponding (5S,7S,7aR)-5,7-disubstituted pyrrolooxazolidine derivatives.

A New Enantioselective Synthesis of trans 2,5-Disubstituted Pyrrolidine Derivatives by Radical Cyclisation

A new and highly enantioselective synthesis of trans 5-substituted 2-hydroxymethylpyrrolidine derivatives is achieved by intramolecular radical cyclization at the 4-position of Δ4,5-oxazolidin-2-one, which leads to C2-symmetrical 2,5-dibenzyloxypyrrolidin-2-one.

Synthesis of Enantiomerically Pure (2R,5R) Disubstituted Pyrrolidines from D-Mannitol

Pyrrolidines 1 and 2 are obtained from D-Mannitol, giving good total yields and in an enantiomerically pure form.Some comments and studies regarding pyrrolidine ring closure (key step) are also reported.

ASYMMETRIC SYNTHESIS OF TRANS-(2R,5R)-BIS(BENZYLOXYMETHYL)PYRROLIDINE

Trans-(2R,5R)-bis(benzyloxymethyl)-pyrrolidine (1) was prepared from 1,2:5,6-diisopropylidene mannitol.Key transformations included the selective protection of primary hydroxy groups and stereocontrolled cyclization.