(2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde

Base Information

Chemical Name:(2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde
CAS No.:192389-28-9
Molecular Formula:C₂₇H₃₇NO₄Si
Molecular Weight:467.681
Hs Code.:

Synonyms:(2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde

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Chemical Property of (2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde

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Technology Process of (2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde

There total 3 articles about (2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde 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: 77.0%

: 192389-30-3
(2S,5R)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate

: 192389-28-9
(2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde

Guidance literature:: (2S,5R)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate; With diisobutylaluminium hydride; In toluene; Petroleum ether; at -78 ℃; for 2.5h;

In toluene; Petroleum ether; at 0 ℃; for 5h; Further stages.;
DOI:10.1016/j.bmc.2007.05.064

Reference yield:

: 192389-29-0
(2S,5S/R)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)methyl-5-methoxy-pyrrolidine

: 192389-28-9
(2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / TMSOTf / CH₂Cl₂ / 0.05 h / -35 °C

2: 66 percent / DIBAH / toluene; petroleum ether; hexane / 1 h / -60 °C

With trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; In hexane; dichloromethane; toluene; Petroleum ether;
DOI:10.1002/chem.200400181

Reference yield:

: 192389-31-4
(2S,5S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-cyanopyrrolidine-1-carboxylate

: 192389-28-9
(2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-pyrrolidine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 54 percent / t-BuOK / toluene; 2-methyl-propan-2-ol / 1.5 h / 0 °C

2: 66 percent / DIBAH / toluene; petroleum ether; hexane / 1 h / -60 °C

With potassium tert-butylate; diisobutylaluminium hydride; In hexane; toluene; Petroleum ether; tert-butyl alcohol;
DOI:10.1002/chem.200400181