(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formyl-3-methoxymethoxymethylpyrrolidine

Base Information

Chemical Name:(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formyl-3-methoxymethoxymethylpyrrolidine
CAS No.:152500-28-2
Molecular Formula:C₂₁H₃₁NO₆
Molecular Weight:393.48
Hs Code.:

Synonyms:(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formyl-3-methoxymethoxymethylpyrrolidine

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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 (2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formyl-3-methoxymethoxymethylpyrrolidine

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Technology Process of (2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formyl-3-methoxymethoxymethylpyrrolidine

There total 22 articles about (2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formyl-3-methoxymethoxymethylpyrrolidine 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: 100.0%

: 152612-43-6
(2S,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formyl-3-methoxymethylpyrrolidine

: 152500-28-2
(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formyl-3-methoxymethoxymethylpyrrolidine

Guidance literature:: With potassium carbonate; In methanol; for 2h; Heating;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield: 63.0%

: 152500-38-4
(2R,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine

: 152500-28-2
(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formyl-3-methoxymethoxymethylpyrrolidine

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃;
DOI:10.1016/S0040-4039(00)73849-4

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 152500-28-2
(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-formyl-3-methoxymethoxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / 4-dimethylaminopyridine / acetonitrile; triethylamine / 3 h / Ambient temperature

2: 99 percent / 3 h / 75 °C

3: 89 percent / 1M hydrochloric acid / tetrahydrofuran; H₂O / 1 h / Ambient temperature

4: 81 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol; acetic acid / 2 h / -10 °C

5: 82 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

6: diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 °C

7: pyridinium p-toluenesulfonate / 3 h / Ambient temperature

8: 69 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

9: 61 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

10: 100 percent / potassium carbonate / methanol / 2 h / Heating

With hydrogenchloride; dmap; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetic acid; triethylamine; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)80643-8