(2R,3S,4S)-N-tert-butoxycarbonyl-3,4-bis(tert-butyldimethylsilyloxy)-2-trityloxymethylpyrrolidine

Base Information

Chemical Name:(2R,3S,4S)-N-tert-butoxycarbonyl-3,4-bis(tert-butyldimethylsilyloxy)-2-trityloxymethylpyrrolidine
CAS No.:165560-20-3
Molecular Formula:C₄₁H₆₁NO₅Si₂
Molecular Weight:704.11
Hs Code.:

Synonyms:(2R,3S,4S)-N-tert-butoxycarbonyl-3,4-bis(tert-butyldimethylsilyloxy)-2-trityloxymethylpyrrolidine

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Chemical Property of (2R,3S,4S)-N-tert-butoxycarbonyl-3,4-bis(tert-butyldimethylsilyloxy)-2-trityloxymethylpyrrolidine

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Technology Process of (2R,3S,4S)-N-tert-butoxycarbonyl-3,4-bis(tert-butyldimethylsilyloxy)-2-trityloxymethylpyrrolidine

There total 4 articles about (2R,3S,4S)-N-tert-butoxycarbonyl-3,4-bis(tert-butyldimethylsilyloxy)-2-trityloxymethylpyrrolidine 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: 76.0%

: 1,1-dimethylethyl N-<(1R,2S,3S)-2,3-bis(tert-butyldimethylsilyloxy)-4-hydroxy-1-trityloxymethylbutylyl>carbamate

: 165560-20-3
(2R,3S,4S)-N-tert-butoxycarbonyl-3,4-bis(tert-butyldimethylsilyloxy)-2-trityloxymethylpyrrolidine

Guidance literature:: With TEA; methanesulfonyl chloride; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.3987/COM-94-7016

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 165560-20-3
(2R,3S,4S)-N-tert-butoxycarbonyl-3,4-bis(tert-butyldimethylsilyloxy)-2-trityloxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 68 percent / imidazole / dimethylformamide / 40 h / Ambient temperature

2: 52 percent / LiBH₄, LiBHEt₃ / diethyl ether; tetrahydrofuran / 0.25 h / Ambient temperature

3: 76 percent / methanesulfonyl chloride, TEA / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; lithium borohydride; TEA; lithium triethylborohydride; methanesulfonyl chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.3987/COM-94-7016

Reference yield:

: 165560-13-4
1,1-dimethylethyl N-<(1R,2S,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methoxycarbonyl-1-trityloxymethylpropanyl>carbamate

: 165560-20-3
(2R,3S,4S)-N-tert-butoxycarbonyl-3,4-bis(tert-butyldimethylsilyloxy)-2-trityloxymethylpyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1: 52 percent / LiBH₄, LiBHEt₃ / diethyl ether; tetrahydrofuran / 0.25 h / Ambient temperature

2: 76 percent / methanesulfonyl chloride, TEA / CH₂Cl₂ / 0.5 h / 0 °C

With lithium borohydride; TEA; lithium triethylborohydride; methanesulfonyl chloride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.3987/COM-94-7016