(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine

Base Information

Chemical Name:(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine
CAS No.:540501-65-3
Molecular Formula:C₂₃H₃₇NO₃SSi
Molecular Weight:435.703
Hs Code.:

Synonyms:(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine

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Chemical Property of (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine

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Technology Process of (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine

There total 8 articles about (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine 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: 73.0%

: 31238-57-0
diphenyl(phenylthiomethyl)phosphine oxide

: 220993-22-6
(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate

: 540501-65-3
(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine

Guidance literature:: diphenyl(phenylthiomethyl)phosphine oxide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃;

(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-oxopyrrolidine-1-carboxylate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 5h;
DOI:10.1021/jo034214l

Reference yield:

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

: 540501-65-3
(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: aqueous Na₂CO₃ / tetrahydrofuran; dioxane / 18 h

2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C

3.1: 11.96 g / NaBH₄ / 1,2-dimethoxy-ethane; H₂O / 0.33 h / Cooling

4.1: 78 percent / TEA; DMAP / CH₂Cl₂

5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH₂Cl₂ / 1 h / 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

6.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C

With 4-methyl-morpholine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; n-butyllithium; TEA; trichloroisocyanuric acid; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; hexane; dichloromethane; water;
DOI:10.1021/jo034214l

Reference yield:

: 61478-26-0
tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

: 540501-65-3
(S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 78 percent / TEA; DMAP / CH₂Cl₂

2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH₂Cl₂ / 1 h / 0 °C

3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

3.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; n-butyllithium; TEA; trichloroisocyanuric acid; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo034214l