141527-78-8

Basic information

• Product Name: BOC-D-SER-OBZL
• Synonyms: BOC-D-SERINE ALPHA-BENZYL ESTER;BOC-D-SERINE BENZYL ESTER;BOC-D-SER-OBZL;N-ALPHA-T-BUTOXYCARBONYL-D-SERINE BENZYL ESTER;N-tert-Butoxycarbonyl-D-serine benzyl ester;(R)-benzyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate;Boc-D-Ser-OBzl Boc-D-Serine benzyl ester;N-[(tert-Butoxy)carbonyl]-D-serine phenylmethyl ester
• CAS NO: 141527-78-8
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.33
• EINECS: 1533716-785-6
• Mol File: 141527-78-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 66-70℃
• Boiling Point: 458.846 °C at 760 mmHg
• Flash Point: 231.302 °C
• Appearance: White/Powder
• Density: 1.174
• Vapor Pressure: 3.25E-09mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.67±0.46(Predicted)
• CAS DataBase Reference: BOC-D-SER-OBZL(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-SER-OBZL(141527-78-8)
• EPA Substance Registry System: BOC-D-SER-OBZL(141527-78-8)

Safety Data

• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 141527-78-8(Hazardous Substances Data)

Usage

Description

BOC-D-SER-OBZL, also known as Boc-D-Serine O-benzyl ester, is a serine derivative featuring N-Boc (tert-butoxycarbonyl) and COOH-benzyl ester protection. This white to off-white powder is a crucial reagent in the synthesis of anti-fungal dilactones, such as UK-2A and UK-3A, due to its unique chemical properties and structural composition.

Uses

Used in Pharmaceutical Industry:
BOC-D-SER-OBZL is used as a reagent for the synthesis of anti-fungal dilactones, specifically UK-2A and UK-3A, which are known for their potent anti-fungal properties. The application reason is to develop new and effective anti-fungal agents to combat various fungal infections.
Used in Organic Chemistry:
BOC-D-SER-OBZL is used as a protected serine derivative in organic chemistry for the synthesis of various biologically active compounds. The application reason is to provide a stable and easily modifiable intermediate for the development of pharmaceuticals and other bioactive molecules.
Used in Research and Development:
BOC-D-SER-OBZL is used as a research compound to study the properties and reactivity of serine derivatives in various chemical reactions. The application reason is to gain a deeper understanding of the chemical behavior of serine derivatives and to explore their potential applications in drug discovery and development.

InChI:InChI=1/C15H21NO5/c1-15(2,3)21-14(19)16-12(9-17)13(18)20-10-11-7-5-4-6-8-11/h4-8,12,17H,9-10H2,1-3H3,(H,16,19)/t12-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 133099-79-3 D-serine benzyl ester 
• 100-39-0 benzyl bromide 
• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 

Downstream Products

• 116611-42-8 (R)-2-tert-butoxycarbonylamino-3-phenylsulfanylpropionic acid methyl ester 
• 1620620-29-2 benzyl (4R)-3-(tert-butyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate 
• 60022-62-0 D-serine benzyl ester hydrochloride 
• 146075-58-3 (2S,6R)-3-Oxo-6-<(phenylmethoxy)carbonyl>-2-piperazineacetic acid methyl ester 
• 145967-52-8 (2S,6S)-6-Methoxycarbonylmethyl-5-oxo-piperazine-1,2,4-tricarboxylic acid 2-benzyl ester 1,4-di-tert-butyl ester 
• 145967-55-1 (2S,6S)-6-Methoxycarbonylmethyl-1-[2-(3-methoxy-phenyl)-acetyl]-5-oxo-piperazine-2-carboxylic acid benzyl ester 
• 145967-53-9 (3S,5S)-5-Methoxycarbonylmethyl-6-oxo-piperazine-1,3-dicarboxylic acid 3-benzyl ester 1-tert-butyl ester 
• 215798-16-6 isobutyric acid (3R,6S,7R,8R)-8-benzyl-3-tert-butoxycarbonylamino-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl ester 
• 210300-16-6 (2R,3R,4S)-2-Benzyl-4-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propionyloxy)-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid 
• 210300-17-7 [(3R,7R,8R,9S)-7-benzyl-8-(tert-butyldimethylsilanyloxy)-9-methyl-2,6-dioxo-[1,5]dioxonane-3-yl]-carbamic acid tert-butyl ester 
• 215798-15-5 ((3R,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-[1,5]dioxonane-3-yl)-carbamic acid tert-butyl ester 
• 215798-12-2 (2R,3R,4S)-2-benzyl-4-((2R)-3-benzyloxy-2-tert-butoxycarbonylaminopropionyloxy)-3-(tert-butyldimethylsilanyloxy)-pentanoic acid benzyl ester 

Relevant articles and documents

Stereoselective synthesis of lanthionine derivatives in aqueous solution and their incorporation into the peptidoglycan of Escherichia coli

The three diastereoisomers - (R,R), (S,S) and meso - of lanthionine were synthesized in aqueous solution with high diastereoselectivity (>99%). The (S) and (R) enantiomers of two differently protected sulfamidates were opened by nucleophilic attack of (R) or (S)-cysteine. Acidification and controlled heating liberated the free lanthionines. Using the same chemistry, an α-benzyl lanthionine was also prepared. The proposed method, which avoids the need of enrichment by recrystallization, opens the way to the labelling of these compounds with 35S. Furthermore, in vivo bioincorporation into Escherichia coli W7 was studied. No incorporation of α-benzyl lanthionine was observed. In contrast, meso-lanthionine can effectively replace meso-diaminopimelic acid in vivo, while in the presence of (R,R)-lanthionine the initial increase of bacterial growth was followed by cell lysis. In the future, meso-[35S]lanthionine could be used to study the biosynthesis of peptidoglycan and its turnover in relation to cell growth and division.

The synthesis of chiral 3-oxo-6-[(phenylmethoxy)-carbonyl]-2-piperazineacetic acid esters designed for the presentation of an aspartic acid side chain. A subsequent novel Friedel Crafts reaction

The syntheses of (2S, 6R)-, and (2S, 6S)-3-oxo-6-[(phenylmethoxy)carbonyl]-2-piperazineacetic acid methyl esters from L- or D-serine and dimethyl-D-malate are described. Acylation of the (2S, 6S) isomer with 3-methoxyphenylacetyl chloride, hydrogenolysis of the benzyl ester, followed by treatment with oxalyl chloride then aluminum chloride led to an unexpected tricyclic product into which a C2O2 unit had been incorporated.