152491-85-5

Usage

Uses

Used in Pharmaceutical Development:
(R)-(+)-N-(TERT-BUTOXYCARBONYL)-Ois used as a protecting group in the pharmaceutical industry for the synthesis of complex molecules. Its ability to mask the reactive hydroxyl group of serine enables chemists to control the stereochemistry of the resulting compounds, which is crucial for the development of effective drugs with minimal side effects.
Used in Materials Science:
In the field of materials science, (R)-(+)-N-(TERT-BUTOXYCARBONYL)-Ois employed as a protecting group to facilitate the synthesis of advanced materials with specific properties. By controlling the reactivity of the hydroxyl group, researchers can create materials with tailored characteristics, such as improved strength, flexibility, or chemical resistance.
Used in Peptide Synthesis:
(R)-(+)-N-(TERT-BUTOXYCARBONYL)-Ois used as a protecting group in peptide synthesis to prevent unwanted side reactions and control the stereochemistry of the resulting peptide. The tert-butoxycarbonyl (Boc) protecting group can be removed under mild conditions, making it a versatile tool for the synthesis of peptides with specific sequences and structures, which are essential for various biological applications and drug development.
Overall, (R)-(+)-N-(TERT-BUTOXYCARBONYL)-Ois a vital component in the development of pharmaceuticals, materials, and other organic compounds due to its ability to protect the reactive hydroxyl group of serine and allow for selective reactions at other functional groups.

InChI:InChI=1/C14H31NO4Si/c1-13(2,3)19-12(17)15-11(9-16)10-18-20(7,8)14(4,5)6/h11,16H,9-10H2,1-8H3,(H,15,17)/t11-/m1/s1

Upstream product

• 126645-26-9 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 176504-16-8 (R)-2-amino-3-((tert-butyldimethylsilyl)oxy)propan-1-ol 
• 70930-18-6 ethyl (S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropanoate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 518986-05-5 O-t-butyldimethylsilyl-N-[(1,1-dimethylethoxy)carbonyl]-N-hydroxymethyl-L-serinal hemiacetal 
• 367490-60-6 (4S)-4-[(t-butyldimethylsilyloxy)methyl]-3-[(1,1-dimethylethoxy)carbonyl]-5-oxazolidinone 
• 123254-10-4 (2S)-2-tert-butoxycarbonylamino-3-(tert-butyldimethylsilanyloxy)propionic acid 
• 518986-06-6 O-t-butyldimethylsilyl-N-[(1,1-dimethylethoxy)carbonyl]-N-hydroxymethyl-L-serinol 

Downstream Products

• 354988-04-8 (2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)-O-(4-methylphenylsulfonyl)propan-1-ol 
• 552332-00-0 C₁₉H₃₃BrN₂O₄Si 
• 950690-19-4 ethyl (S)-5-((tert-butoxycarbonyl)amino)cyclohexa-1,3-diene-1-carboxylate 
• 90242-16-3 (5S)-5-<(tert-butoxycarbonyl)amino>cyclohexadienecarboxylic acid 
• 903907-79-9 tert-butyl (R)-4-((S)-11,11-dimethyl-7-methylene-3-oxo-1,10,10-triphenyl-2,9-dioxa-4-aza-10-sila dodecan-5-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 903907-78-8 tert-butyl (4R)-4-((5S)-7-hydroxy-11,11-dimethyl-3-oxo-1,10,10-triphenyl-2,9-dioxa-4-aza-10-siladodecan-5-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 903907-77-7 (4R)-((1S)-benzyloxycarbonylamino-3,4-dihydroxybutyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 179472-13-0 2-[(tert-butyloxycarbonyl)amino]-3-[N₃-benzoyl(thymin-1-yl)]-L-propan-1-ol 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 1338090-99-5 [(R)-2-(2-bromophenyl)-1-(tert-butyl-dimethylsilanyloxymethyl)ethyl]carbamic acid tert-butyl ester 
• 1034774-67-8 methyl (7R)-7-[(tert-butoxycarbonyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate 
• 1034774-66-7 tert-butyl (R)-2-((4-nitrophenylsulfonyloxy)methyl)aziridine-1-carboxylate 

Relevant academic research and scientific papers

Synthesis of an (R)-Garner-type aldehyde from L-serine: Useful building block for a (+)-furanomycin derivative

(+)-Furanomycin is an antibiotic that substitutes for L-isoleucine in bacterial protein translation. We propose here a new short synthesis of a useful intermediate, a 1,2-diprotected 2-aminopent-4-ene-1,3-diol, starting from the inexpensive natural amino acid L-serine, and via a Garner-type aldehyde. The (R)-α-amino aldehyde was obtained by the construction of an oxazoline ring between the N-protected amino group and the hydroxy group that resulted from reduction of the carboxylic acid functionality of L-serine. Georg Thieme Verlag Stuttgart.

Simple molecular engineering of glycol nucleic acid: Progression from self-pairing to cross-pairing with cDNA and RNA

The acyclic chiral nucleic acid analogue, Glycol Nucleic Acid (GNA), displayed exceptional structural simplicity and atom economy while forming self-paired duplexes, using canonical Watson-Crick base pairing. We disclose here that the replacement of phosp

Application of the highly sensitive labeling reagent to the structural confirmation of readily isomerizable peptides

Thioamycolamide A (1) is a biosynthetically unique cytotoxic cyclic microbial lipopeptide that bears a d-configured thiazoline, a thioether bridge, a fatty acid side chain, and a reduced C-terminus. It has gained attention for its unique structure, and very recently we reported the total synthesis of 1 via a biomimetic route. The NMR spectra of synthetic 1 agreed with those of natural 1. However, structural identity between peptidic natural and synthetic compounds is often difficult to confirm by comparison of NMR spectra because their NMR spectra vary depending on the conditions in the NMR tube, which often result in the structural misassignment of peptidic compounds. Especially, our total synthesis based on the putative biomimetic route potentially gives 1 as a diastereomixture at the final step. The problem is that the diastereomers of peptidic mid-sized molecules often exhibit similar properties (such as NMR spectra and bioactivities), and their separation procedures are often laborious. Herein we report the structural confirmation of synthetic 1 by the LC–MS-based chromatographic comparison with the use of our highly sensitive labeling reagent l-FDVDA; the highly sensitive-advanced Marfey’s method (HS-advanced Marfey’s method). This work demonstrated the utility of our highly sensitive labeling reagent for the structural determination of not only scarce natural products but also readily isomerizable synthetic compounds.

COMPOUNDS FOR TREATING FAMILIAL DYSAUTONOMIA

The present description relates to compounds useful for improving pre-mRNA splicing in a cell. In particular, another aspect of the present description relates to substituted thieno [3,2-d]pyrimidine compounds, forms, and pharmaceutical compositions there

CYCLIC COMPOUNDS AND METHODS OF USING SAME

The present application relates to compounds of Formula (I), as defined herein, and pharmaceutically acceptable salts thereof. The present application also describes pharmaceutical composition comprising a compound of Formula (I), and pharmaceutically acc

THIOENO[3,2-B] PYRIDIN-7-AMINE COMPOUNDS FOR TREATING FAMILIAL DYSAUTONOMIA

The present description relates'to compounds of formula (I) useful for improving pre-mRNA splicing in a cell. In particular, another aspect of the present description relates to substituted thieno[3,2-b]pyridine compounds, forms, and pharmaceutical compos

MACROCYCLIC KINASE INHIBITORS AND THEIR USE

The present disclosure relates to certain chiral diaryl macrocyclic derivatives, pharmaceutical compositions containing them, and methods of using them to treat cancer, pain, neurological diseases, autoimmune diseases, and inflammation.

PROCESS FOR PREPARATION OF SACUBUTRIL INTERMEDIATE

The present application relates to a process for preparation of tert-butyl (R)-(1-([1,1'-biphenyl]-4- yl)-3-hydroxypropan-2-yl)carbamate (IA). The compound of formula (IA) may be used as an intermediate for the preparation of sacubitril.

Morita-Baylis-Hillman approach toward formal total synthesis of tamiflu and total synthesis of gabaculine

A Morita-Baylis-Hillman reaction mediated approach to the formal total synthesis of oseltamivir and the total synthesis of gabaculine is described. This strategy involves the enantiocontrolled preparation of Corey's intermediate in 22 % yield, which is pr

A stereodivergent route to four stereoisomeric 3′- acetoxycyclopentenylglycine derivatives

A short and efficient synthetic route to four stereoisomeric 3-acetoxycyclopentenylglycine derivatives from l-serine has been developed. The method features a stereoselective conjugate addition and ring-closing metathesis as key steps. Georg Thieme Verlag Stuttgart · New York.