156627-42-8

Basic information

• Product Name: Carbamic acid, [3-hydroxy-1-(hydroxymethyl)propyl]-, 1,1-dimethylethyl ester
• Synonyms: Carbamic acid, [3-hydroxy-1-(hydroxymethyl)propyl]-, 1,1-dimethylethyl ester;tert-Butyl (1,4-dihydroxybutan-2-yl)carbamate
• CAS NO: 156627-42-8
• Molecular Formula: C9H19NO4
• Molecular Weight: 205.25146
• Product Categories: N-BOC
• Mol File: 156627-42-8.mol
• Article Data: 32

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, [3-hydroxy-1-(hydroxymethyl)propyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [3-hydroxy-1-(hydroxymethyl)propyl]-, 1,1-dimethylethyl ester(156627-42-8)
• EPA Substance Registry System: Carbamic acid, [3-hydroxy-1-(hydroxymethyl)propyl]-, 1,1-dimethylethyl ester(156627-42-8)

Safety Data

• Hazardous Substances Data: 156627-42-8(Hazardous Substances Data)

Usage

Uses

tert-Butyl (1,4-Dihydroxybutan-2-yl)carbamate is a reagent used in the synthesis of oxadiazole oxime derivatives as oxygenase inhibitors as well as triazoles.

Upstream product

• 146514-35-4 (RS)-N-tert-butoxycarbonyl-α-amino-γ-butyrolactone 
• 130622-08-1 (2R)-2-tert-butoxycarbonylamino-succinic acid dimethyl ester 
• 67198-86-1 (R)-2-[(tert-butoxycarbonyl)amino]butano-4-lactone 
• 13726-67-5 Boc-Asp-OH 
• 24424-99-5 di-tert-butyl dicarbonate 
• 130622-08-1 dimethyl N-tert-butoxycarbonyl-L-aspartate 
• 128427-09-8 (S)-N-tert-butoxycarbonyl-aspartic acid diethyl ester 
• 10405-07-9 (2S)-2-amino-1,4-butanediol 
• 56-84-8 L-Aspartic acid 
• 428440-11-3 D-Boc-L-Asp(OEt)OEt 

Downstream Products

• 201404-86-6 tert-butyl (4R)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 852874-60-3 (S)-tert-butyl 1-methylpyrrolidin-3-ylcarbamate 
• 40856-59-5 tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate 
• 104227-71-6 N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester 
• 1048703-14-5 (R)-tert-butyl (4-hydroxy-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate 
• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
• 153053-19-1 (4R)-2,2-dimethyl-4-(2-oxoethyl)-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

Synthesis of Aminomethylene- gem-bisphosphonates Containing an Aziridine Motif: Studies of the Reaction Scope and Insight into the Mechanism

A broad range of N-carbamoylaziridines were obtained and then treated by the diethyl phosphonate anion to afford α-methylene-gem-bisphosphonate aziridines. Study of the reaction's scope and additional experiments indicates that the transformation proceeds via a new mechanism involving the chelation of lithium ion. This last step is crucial for the reaction to occur and disfavors the aziridine ring-opening. A phosphonate-phosphate rearrangement from a α-hydroxybisphosphonate aziridine intermediate is also proposed for the first time. This reaction provides a simple and convenient method for the synthesis of a highly functionalized phosphonylated aziridine motif.

β-Hydroxy- A nd β-Aminophosphonate Acyclonucleosides as Potent Inhibitors of Plasmodium falciparum Growth

Malaria is an infectious disease caused by a parasite of the genus Plasmodium, and the emergence of parasites resistant to all current antimalarial drugs highlights the urgency of having new classes of molecules. We developed an effective method for the synthesis of a series of β-modified acyclonucleoside phosphonate (ANP) derivatives, using commercially available and inexpensive materials (i.e., aspartic acid and purine heterocycles). Their biological evaluation in cell culture experiments and SAR revealed that the compounds' effectiveness depends on the presence of a hydroxyl group, the chain length (four carbons), and the nature of the nucleobase (guanine). The most active derivative inhibits the growth of Plasmodium falcIParum in vitro in the nanomolar range (IC50 = 74 nM) with high selectivity index (SI > 1350). This compound also showed remarkable in vivo activity in P. berghei-infected mice (ED50 ～0.5 mg/kg) when administered by the IP route and is, although less efficient, still active via the oral route. It is the first ANP derivative with such potent antimalarial activity and therefore has considerable potential for development as a new antimalarial drug.

Preparation method of sitagliptin intermediate

The invention discloses a preparation method of a sitagliptin intermediate and belongs to the field of medicine synthesis. The invention provides a preparation method of a compound 2; the compound 2 is prepared without the need of a catalyst and a resolving agent which have a high price and harsh low-temperature conditions, so that the cost is reduced to the great extent; the preparation method has the advantages of simple technology, high purity and high yield and is suitable for mass production.