(2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine

Base Information

• Chemical Name: (2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine
• CAS No.: 27958-05-0
• Molecular Formula: C₂₀H₂₃NO₅
• Molecular Weight: 357.406
• Mol file: 27958-05-0.mol

Synonyms:(2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine

Chemical Property of (2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine

There total 16 articles about (2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 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: 72.0%

(2R,3S,4S)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine (27958-06-1,604789-37-9,604789-40-4,736097-79-3) + benzyl chloroformate (501-53-1,94274-21-2) → (2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine (27958-05-0)

Guidance literature:

With sodium carbonate; In dichloromethane; water; for 2.5h; Ambient temperature;

DOI:10.1021/jo00357a023

Reference yield:

(3R,4R)-1-Benzyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-5-(4-methoxy-benzyl)-pyrrolidin-2-one → (2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine (27958-05-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Et₃SiH, BF*Et₂O, 2.) concd. HCl / 1.) CH₂Cl₂, 0 deg C, 2.) MeOH

2: 1.) LiAlH₄, 2.) H₂ / 2.) Pd (black) / 1.) THF, RT

3: NaHCO₃ / methanol

With hydrogenchloride; triethylsilane; lithium aluminium tetrahydride; BF*Et₂O; hydrogen; sodium hydrogencarbonate; palladium; In methanol;

DOI:10.3987/COM-95-7214

Reference yield:

(3R,4S,5R)-N-Benzyl-3,4-dihydroxy-5-p-anisyl-pyrrolidon-2 (23006-20-4) → (2R,3S,4S)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine (27958-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LiAlH₄, 2.) H₂ / 2.) Pd (black) / 1.) THF, RT

2: NaHCO₃ / methanol

With lithium aluminium tetrahydride; hydrogen; sodium hydrogencarbonate; palladium; In methanol;

DOI:10.3987/COM-95-7214

upstream raw materials:

(2R,3S,4S)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine

benzyl chloroformate

(3R,4S,5R)-N-Benzyl-3,4-dihydroxy-5-p-anisyl-pyrrolidon-2

(3R,4S,5R)-1-Benzyl-3,4-bis-benzyloxy-5-(4-methoxy-benzyl)-pyrrolidin-2-one

Downstream raw materials:

(2R,3S,4S)-N-(benzyloxycarbonyl)-3-hydroxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine