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

Base Information

Chemical Name:(2S,3R,4R)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine
CAS No.:111765-92-5
Molecular Formula:C₂₀H₂₃NO₅
Molecular Weight:357.406
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

There total 20 articles about (2S,3R,4R)-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: 93.0%

: 19713-95-2,22862-73-3,27958-06-1,604789-37-9,604789-40-4,736097-79-3
(2S,3R,4R)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine

: 501-53-1,94274-21-2
benzyl chloroformate

: 111765-92-5
(2S,3R,4R)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine

Guidance literature:: With sodium hydrogencarbonate; In methanol; dichloromethane; at 40 ℃; for 2.5h; Inert atmosphere;
DOI:10.1016/j.carres.2020.107988

Reference yield:

: 869660-95-7
1-O-benzyl-2,3-O-isopropylidene-4-oxiranyl-D-arabinitol

: 111765-92-5
(2S,3R,4R)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine

Guidance literature:: Multi-step reaction with 10 steps

1.1: magnesium; iodine / tetrahydrofuran

1.2: 86 percent / copper(I) iodide / tetrahydrofuran / 0 - 20 °C

2.1: triethylamine / CH₂Cl₂ / 1 h / 20 °C

3.1: 550 mg / sodium azide; 18-crown-6 / dimethylsulfoxide / 24 h / 65 °C

4.1: LiAlH₄ / tetrahydrofuran / 0 - 20 °C

5.1: 450 mg / triethylamine / tetrahydrofuran / 6 h / 20 °C

6.1: 83 percent / lithium; liq. ammonia / tetrahydrofuran / 0.5 h / -78 °C

7.1: triethylamine / CH₂Cl₂ / 1 h / 20 °C

8.1: trifluoroacetic acid / CH₂Cl₂; H₂O / 10 h / 20 °C

9.1: triethylamine / methanol / 5 h / 20 °C

10.1: 58 mg / sodium carbonate / tetrahydrofuran / 2 h / 20 °C

With lithium aluminium tetrahydride; sodium azide; 18-crown-6 ether; ammonia; iodine; lithium; sodium carbonate; magnesium; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; 1.2: Crignard reaction;
DOI:10.1016/j.tetasy.2005.08.039

Reference yield:

: Methanesulfonic acid (2R,3R,4S)-4-amino-2,3-dihydroxy-5-(4-methoxy-phenyl)-pentyl ester

: 111765-92-5
(2S,3R,4R)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / methanol / 5 h / 20 °C

2: 58 mg / sodium carbonate / tetrahydrofuran / 2 h / 20 °C

With sodium carbonate; triethylamine; In tetrahydrofuran; methanol;
DOI:10.1016/j.tetasy.2005.08.039