344884-10-2

Usage

Uses

Used in Organic Synthesis:
Tert-butyl 2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate is used as a versatile building block for the synthesis of various organic molecules due to its unique structure and functional groups.
Used in Pharmaceutical Research:
Tert-butyl 2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate is used as a precursor in the development of new drugs because of its potential pharmacological activities and its ability to be modified for specific applications.
Used in Chemical Synthesis as a Protective Group:
The tert-butyl group in tert-butyl 2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate provides stability and protection to the reactive sites, making it a valuable intermediate for protecting functional groups during chemical synthesis.

Upstream product

• 128811-31-4 tert-butyl (2R)-2-<<(tert-butyl)dimethylsilyloxy>methyl>-5-oxopyrrolidine-1-carboxylate 
• 4042-36-8 D-pyrrolidone-5-carboxylic acid 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 141393-87-5 4-<(tert-butoxycarbonyl)amino>-6,7-O-isopropylidene-2,3,4-trideoxy-L-arabino-hept-2-enonic acid 1,4-lactam 
• 185303-86-0 N-(tert-butoxycarbonyl)-6,7-O-isopropylidene-2,3-dideoxy-L-arabinoheptono-1,4-lactam 
• 56-86-0 L-glutamic acid 
• 185303-76-8 tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate 
• 141393-83-1 (4S,5S,6R)-N-(tert-butoxycarbonyl)-6,7-O-isopropylidene-2,3-dideoxy-hept-2-enono-1,4-lactam 
• 141293-14-3 N-(tert-butoxycarbonyl)pyrrol-2(5H)-one 
• 141293-28-9 N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 
• 17342-08-4 (S)-Pyroglutaminol 
• 106191-02-0 (S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one 
• 132974-83-5 (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 128811-31-4 tert-butyl (2R)-2-<<(tert-butyl)dimethylsilyloxy>methyl>-5-oxopyrrolidine-1-carboxylate 
• 81658-27-7 (S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 128811-44-9 tert-butyl N-<(1R)-1-<<(4-methylphenyl)sulfonyloxy>methyl>-4-oxo-4-phenylbutyl>carbamate 

Relevant academic research and scientific papers

Rhodium-Catalyzed Stereospecific C?H Amination for the Construction of Spiroaminal Cores: Reactivity Difference between Nitrenoid and Carbenoid Species against Amide Functionality

Metal nitrenoids and metal carbenoids exhibit similar reactivity for insertion into a C?H bond and a C=C double bond. These reactions have attracted the attention of organic chemists due to their unusual bond-forming ability, but the reactivity difference between these chemical species has not been studied. In this paper, we examined the reactivity difference using the corresponding Rh nitrenoid and Rh carbenoid precursors. The Rh nitrenoid inserted into an intramolecular C(sp3)?H bond adjacent to an amide nitrogen, affording functionalized spiroaminals that are ubiquitous in natural products, while the Rh carbenoid inserted into an amide C?N bond. The totally different reactivity was rationalized by the relatively low energy barrier for the C?H insertion reaction of the Rh nitrenoid. Computational analysis suggests that the origin of the discrepancy is the electrophilicity of the coordinating atoms to the Rh complex.

Discovery of an 8-aza-5-thiaProstaglandin E1 analog as a highly selective EP4 receptor agonist

For the purpose of discovering an orally available EP4 subtype-selective agonist, a series of 8-aza prostaglandin E1 (PGE1) analogs were synthesized and evaluated for their affinity for PGE2 receptor subtypes. Additionally

Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol.

[figure: see text] Cleavage of an O-silyl ether in an N-BOC-protected pyroglutaminol using TBAF led to an unprecedented migration of the BOC group. An investigation of the mechanism, based on experimental data and quantum mechanical calculations, is presented. Similar migration was observed for N-Cbz and N-methoxycarbonyl groups.

Lewis acid assisted vinylogous Mannich and Mukaiyama aldol reactions: A route to densely hydroxylated indolizidine alkaloid analogues

The hydroxymethyl-substituted indolizidines 6 and 7, representative members of a ring-B-expanded alexine-australine subclass, are readily accessible by starting with furan-based silyloxydiene 12 and hydroxymethyl hemiaminal 11, through a synthesis sequence involving a scantily exploited vinylogous version of the Mannich reaction. The key iminium electrophilic acceptor 11 is, in turn, available through a vinylogous intermolecular Mukaiyama aldolization process between pyrrole-based silyloxydiene 8 and (S)- glyceraldehyde 9.

Expeditious syntheses of sugar-modified nucleosides and collections thereof exploiting furan-, pyrrole-, and thiophene-based siloxy dienes

A series of individual sugar-modified pyrimidine nucleosides including enantiomerically enriched 2',3'-dideoxynucleosides 14a-c (α and β anomers of L- and D-series), 2',3'-dideoxy-4'-thionucleosides 21a-c (α and β anomers of L- and D-series), and 2',3'-dideoxy-4'-azanucleosides 28a-c (β anomers of L- and D-series) were synthesized, with uniform chemistry and high stereochemical efficiency, exploiting a triad of versatile heterocyclic siloxy dienes, namely, 2-(tert-butyldimethylsiloxy)furan (TBSOF), 2-(tert- butyldimethylsiloxy)thiophene (TBSOT), and N-(tert-butoxycarbonyl)-2-(tert- butyldimethylsiloxy)pyrrole (TBSOP). The synthetic procedure advantageously used both enantiomers of glyceraldehyde acetonide (D-1 and L-1) as sources of chirality and as synthetic equivalents of the formyl cation. The outlined chemistry also allowed for the rapid assemblage of a 30-member collection of racemic nucleosides (D,L-L) as well as one 15-member ensemble of chiral analogues (L-L), along with some related sublibraries.

Total syntheses of N-boc-protected 3′-deoxy-4′-azathymidine and 4′-azauridine

Novel modified nucleosides 4, 11, ent-11, and 17, wherein the furanose ring oxygen is replaced by nitrogen, have been synthesized by reacting azasugars 3, 10, ent-10, and 15 with silylated uracil or thymine bases.

Synthesis of (3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxyme thyl-2-pyrrolidinone from (S)-pyroglutaminol

(3R,4R,5R)-1-(tert-Butoxycarbonyl)-3,4-isopropylidenedioxy-5-methoxyme thyl-2-pyrrolidinone (6), a useful chiral intermediate for the preparation of calyculins, was synthesized starting from (S)-pyroglutaminol via the O-methylation of 1c with diazomethane in the presence of fluoboric acid and cis-dihydroxylation of the α,β-unsaturated lactam (4) as the key reactions.

12. Approaches to the Synthesis of Cytochalasans; Part 9: A Versatile Concept Leading To All Structural Types of Cytochalasans

Starting from D-glutamic acid (5), the bicyclic compounds 4a and 4b were synthesized via 17 (Schemes 1 and 2).The reaction leading to 4g and 4h with LiCuPh2 was not successful.But treatment of the N-protected model lactams 19, 21, and 22 with Li2Cu(CN)Ph2 gave the amino ketones 24, 26, and 26, respectively (Scheme 3).The desired compound 23 was obtained from 20.Conversion of the unprotected lactams 28, 31, and 32 gave the phenyl derivative 34 in excellent yields.Ester 35 was transformed to the α-amino-γ-oxo-acid derivative 36.This conversion opens a novel access to this type of compounds.