58577-87-0

Basic information

• Product Name: (R)-2-AMINO-3-BENZYLOXY-1-PROPANOL
• Synonyms: O-BENZYL-D-SERINOL;O-BENZYL-L-SERINOL;SERINOL(BZL);(R)-(+)-2-AMINO-3-BENZYLOXY-1-PROPANOL;(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL;H-D-SER(BZL)-OL;H-SER(BZL)-OL;Serinol(Bzl)·HCl
• CAS NO: 58577-87-0
• Molecular Formula: C₁₀H₁₅NO₂
• Molecular Weight: 181.23
• Product Categories: Amino Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 58577-87-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: 34-37 °C(lit.)
• Boiling Point: 307 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.0918 (rough estimate)
• Vapor Pressure: 3.44E-05mmHg at 25°C
• Refractive Index: 1.5464 (estimate)
• Storage Temp.: Store at 0-5°C
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• PKA: 12.53±0.10(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: (R)-2-AMINO-3-BENZYLOXY-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-AMINO-3-BENZYLOXY-1-PROPANOL(58577-87-0)
• EPA Substance Registry System: (R)-2-AMINO-3-BENZYLOXY-1-PROPANOL(58577-87-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: 3267
• WGK Germany: 3
• HazardClass: 8
• Hazardous Substances Data: 58577-87-0(Hazardous Substances Data)

Usage

Uses

(R)-(+)-2-Amino-3-benzyloxy-1-propanol is used as a reagent to synthesize beta-amino alcohols, compounds that are used as therapeutic agents to treat heart disease. (R)-(+)-2-Amino-3-benzyloxy-1-propanol is also used as a reagent to synthesize 15-membered macrolide antibiotics, drugs that are used to treat respiratory tract infections.

InChI:InChI=1/C10H15NO2/c11-10(6-12)8-13-7-9-4-2-1-3-5-9/h1-5,10,12H,6-8,11H2/t10-/m1/s1

Upstream product

• 46460-82-6 O-benzyl-L-serine methyl ester 
• 10433-52-0 O-benzyl-D-serine 
• 4726-96-9 O-Benzyl-L-serine 
• 1336-21-6 ammonium hydroxide 
• 60-29-7 diethyl ether 
• 194861-65-9 methyl O-benzyl-N-trityl-L-serinate 
• 80963-10-6 methyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 133099-79-3 D-serine benzyl ester 

Downstream Products

• 158612-99-8 (4S)-4-[(benzyloxy)methyl]-1,3-oxazolidin-2-one 
• 131833-93-7 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] 
• 883442-60-2 (R)-3-benzyloxy-2-[(S)-2,2-bis-(2,2-dimethylpropoxy)-1-methylethylamino]-propan-1-ol 
• 883442-59-9 (R)-3-benzyloxy-2-[(R)-2,2-bis-(2,2-dimethylpropoxy)-1-methylethylamino]-propan-1-ol 
• 1189332-00-0 (5S)-5-[(benzyloxy)methyl]-[1,3,4]-oxathiazinane-3,3-dioxide 
• 1189331-99-4 (1R)-N-[(2-benzyloxy)-1-(hydroxymethyl)ethyl]chloromethane sulphonamide 
• 1198016-20-4 (2R)-2-{[6-(methyloxy)-3-nitro-2-pyridinyl]amino}-3-[(phenylmethyl)oxy]-1-propanol 
• 937400-28-7 (5S)-5-[(benzyloxy)methyl]morpholin-3-one 
• 1207625-90-8 (5S)-5-[(benzyloxy)methyl]-4-methylmorpholin-3-one 
• 1189332-01-1 (1R)-N-benzyl-N-[2-(benzyloxy)-1-(hydroxymethyl)ethyl]-1-chloromethane sulphonamide 
• 1043498-11-8 (S)-4-benzyloxymethyl-4,5-dihydrooxazol-2-ylamine 

Relevant articles and documents

Diverse synthetic approaches towards C1′-branched acyclic nucleoside phosphonates

Acyclic nucleoside phosphonates (ANPs) represent a significant class of antiviral, anticancer, and antiprotozoal compounds. It is therefore highly desirable to have diverse synthetic routes leading towards these molecules. In the past, many structural modifications were explored, but surprisingly, the field of C1′-branched ANPs has been neglected with only a handful of articles reporting their synthesis. Herein we describe and compare five convenient approaches leading to key synthetic 6-chloropurine ANPs bearing the 9-phosphonomethoxyethyl (PME) moiety branched at the C1′ position. These intermediates can be further vastly diversified into target C1′-branched ANPs bearing either natural or unnatural nucleobases. The importance of C1′-branched ANPs is emphasized by their analogy with C1′-substituted cyclic nucleotides (such as remdesivir, a broad-spectrum antiviral agent) and evaluation of their biological activity (e.g. antiviral, antineoplastic, and antiprotozoal) will be a tempting subject of further research.

Synthesis and structure-activity relationship of a novel class of 15-membered macrolide antibiotics known as '11a-azalides'

Macrolide antibiotics are widely prescribed for the treatment of respiratory tract infections; however, the increasing prevalence of macrolide-resistant pathogens is a public health concern. Therefore, the development of new macrolide scaffolds with activities against resistant pathogens is urgently needed. An efficient method for reconstructing the erythromycin A macrolactone skeleton has been established. Based on this methodology, novel 15-membered macrolides, known as '11a-azalides', with substituents at the C12, C13, or C4″ positions were synthesized and their antibacterial activities were evaluated. These derivatives showed promising antibacterial activities against erythromycin-resistant Streptococcus pneumoniae. Among them, the C4″ substituted derivatives had the most potent activity against erythromycin-resistant S. pneumoniae.

Cyclic sulfur ylides derived from gleason-type chiral auxiliaries for the asymmetric synthesis of epoxy amides

Gleason-type chiral auxiliaries were used for the synthesis of a novel class of sulfonium salts, obtained via methylation of the sulfide with Meerwein's salt. The salts were reacted with aldehydes under basic conditions to provide epoxy amides, which were reduced to their corresponding epoxy alcohols in excellent enantiomeric excesses. Interestingly, it was feasible to synthesize both enantiomeric epoxy alcohols depending on which of the sulfonium salts, prepared from L-amino acids (6 and 9 from L-valine or 15 and 16 from L-serine) was employed.