128427-10-1

Basic information

• Product Name: (S)-(-)-2-(Boc-Amino)-1,4-butanediol
• Synonyms: (S)-(-)-N-Boc-2-Amino-1,4-butanediol;Carbamic acid, [(1S)-3-hydroxy-1-(hydroxymethyl)propyl]-, 1,1-dimethylethyl;(S)-(-)-2-(boc-Amino)-1,4-butendiol;(S)-N-BOC-2-AMINO-BUTANE-1,4-DIOL ;(S)-TERT-BUTYL 1,4-DIHYDROXYBUTAN-2-YLCARBAMATE;(S)-N-BOC-2-AMINO-BUTANE-1,4-DIOL ,97%;(S)-(-)-2-(Boc-Amino)-1,4-butanediol;(S)-(3-Hydroxy-1-hydroxymethylpropyl)carbamic acid tert-butyl ester
• CAS NO: 128427-10-1
• Molecular Formula: C₉H₁₉NO₄
• Molecular Weight: 205.25
• Product Categories: N-BOC;API intermediates;Amino Alcohols;Chiral Building Blocks;Organic Building Blocks;Chiral Compounds
• Mol File: 128427-10-1.mol
• Article Data: 26

Chemical Properties

• Melting Point: 65-69 °C(lit.)
• Boiling Point: 365 °C at 760 mmHg
• Flash Point: 174.6 °C
• Appearance: White/Crystalline Powder
• Density: 1.11 g/cm³
• Vapor Pressure: 8.28E-07mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: 2-8°C
• PKA: 11.81±0.46(Predicted)
• CAS DataBase Reference: (S)-(-)-2-(Boc-Amino)-1,4-butanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-2-(Boc-Amino)-1,4-butanediol(128427-10-1)
• EPA Substance Registry System: (S)-(-)-2-(Boc-Amino)-1,4-butanediol(128427-10-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 128427-10-1(Hazardous Substances Data)

Usage

Chemical Properties

whitecrystallinepowde

Uses

(S)-(?)-2-(Boc-amino)-1,4-butanediol can be used as a reactant to synthesize:Thiourea-based organocatalysts for asymmetric Michael addition reactions of nitroalkenes to α-nitrocyclohexanone.Bis-copper (II) complex based catalysts for enantioselective Michael reactions.

InChI:InChI=1/C9H19NO4/c1-9(2,3)14-8(13)10-7(6-12)4-5-11/h7,11-12H,4-6H2,1-3H3,(H,10,13)/t7-/m0/s1

Upstream product

• 10405-07-9 (2S)-2-amino-1,4-butanediol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 128427-09-8 (S)-N-tert-butoxycarbonyl-aspartic acid diethyl ester 
• 56-84-8 L-Aspartic acid 
• 146514-35-4 (RS)-N-tert-butoxycarbonyl-α-amino-γ-butyrolactone 
• 130622-08-1 dimethyl N-tert-butoxycarbonyl-L-aspartate 
• 13726-67-5 Boc-Asp-OH 

Downstream Products

• 852874-60-3 (S)-tert-butyl 1-methylpyrrolidin-3-ylcarbamate 
• 1619261-23-2 (S)-tert-butyl-(2-(2-tosyloxy)ethyl)aziridine-1-carboxylate 
• 1619261-28-7 (R)-3-(tert-butoxycarbonyl)-2,2,2-trifluoro-acetamido-4-(3-methoxyphenyl)butyl 4-methylbenzenesulfonate 
• 1619261-36-7 (R)-4-(3-methoxybenzyl)-1,3-oxazinan-2-one 
• 1619261-25-4 (R)-3-(tert-butoxycarbonylamino)-4-(3-methoxyphenyl)butyl 4-methylbenzenesulfonate 
• 1619261-38-9 (R)-tert-butyl 4-hydroxy-1-(3-methoxy-phenyl)butan-2-ylcarbamate 
• 1619261-32-3 (R)-tert-butyl 4-iodo-1-(3-methoxyphenyl)-butan-2-yl(2,2,2-trifluoroacetyl)carbamate 
• 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 
• 205491-16-3 (S)-tert-butyl (4-((tert-butyldiphenylsilyl)oxy)-1-hydroxybutan-2-yl)carbamate 

Relevant articles and documents

JM-PHOS ligands: Second-generation phosphine oxazolines for asymmetric catalysis

(formula presented) A small library of phosphine oxazollne ligands 2 was prepared and tested in palladium-mediated allylation processes (reactions 1 and 2). They were found to be superior to the first-generation ligands 1 and as effective as the well-know

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.

Design and synthesis of a novel site-directed reducing agent for the disulfide bond involved in the acetylcholine binding site of the AChoR

The 2-trimethylammonioethyloxycarbonylamino-1,4-butanedithiol 7 was synthesized and tested as a site-directed reducing agent for the disulfide bond involved in the acetylcholine binding site of the AChoR, which was then specifically labeled by an undecagold cluster.

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.