135042-17-0

Basic information

• Product Name: N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER
• Synonyms: N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER;(2R,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate;(2R,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate;(2R,4S)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-Methyl ester (N-Boc-trans-4-Hydroxy-D-proline Methyl ester;1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-diMethylethyl) 2-Methyl ester, (2R,4S)-;Boc-trans-4-Hydroxy-D-proline Methyl ester;N-tert-butoxycarbonyl-trans-4-hydroxy-D-proline Methyl ester;(2R,4S)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• CAS NO: 135042-17-0
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.28
• EINECS: 1592732-453-0
• Mol File: 135042-17-0.mol
• Article Data: 64

Chemical Properties

• Boiling Point: 335.244 °C at 760 mmHg
• Flash Point: 156.55 °C
• Appearance: /
• Density: 1.216±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 8.47E-06mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: 2-8°C
• PKA: 14.27±0.40(Predicted)
• CAS DataBase Reference: N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER(135042-17-0)
• EPA Substance Registry System: N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER(135042-17-0)

Safety Data

• Hazardous Substances Data: 135042-17-0(Hazardous Substances Data)

Usage

General Description

"N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER" is a chemical compound that consists of a trans-4-hydroxy-D-proline core with a methyl ester modification and a tert-butoxycarbonyl (Boc) protecting group. It is commonly used in the synthesis of peptides and other organic molecules. The Boc protecting group helps to prevent unwanted reactions during the synthesis process, while the methyl ester modification allows for easy manipulation of the compound. This chemical is important in the field of medicinal chemistry and drug development, as it can be used to create new pharmaceutical compounds with potentially beneficial properties.

InChI:InChI=1/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m0/s1

Upstream product

• 148017-37-2 (2S,4S)-1-t-butoxycarbonyl-4-formyloxy-2-methoxycarbonylpyrrolidine 
• 168264-25-3 Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 81102-38-7 cis-L-hydroxyproline methyl ester 
• 67-56-1 methanol 
• 87250-97-3 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 
• 188109-82-2 (2S,4S)-1-tert-butyl 2-methyl 4-acetoxypyrrolidine-1,2-dicarboxylate 
• 121147-94-2 1-tert-butyl 2-methyl (2S,4S)-4-((benzoyl)oxy)-1,2-pyrrolidinedicarboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 186581-53-3 diazomethane 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 102195-80-2 (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate 
• 168264-26-4 (2S,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 198969-21-0 (2R,4R)-4-(4-Chloro-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 198969-19-6 (2R,4R)-1-tert-butyl 2-methyl 4-phenoxypyrrolidine-1,2-dicarboxylate 
• 244786-53-6 N-Boc-L-trans-Pro(4-<4-<(E)-2-(4-cyanophenyl)-1-diazenyl>phenoxy>)-OMe 
• 146060-25-5 O2-methyl O1-tert-butyl (2S,4S)-4-(p-tolylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 
• 121147-97-5 1-tert-butyl 2-methyl (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate 
• 438452-29-0 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromo-phenyl)sulfonyl]oxy}-pyrrolidine-1,2-dicarboxylate 
• 169032-99-9 (2S,4S)-4-Chloro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 629616-71-3 1-(1,1-dimethylethyl) 2-methyl (2R,4S)-4-{[(4-nitrophenyl)sulfonyl]oxy}-2,3,4,5-tetrahydro-1H-pyrrole-1,2-dicarboxylate 
• 433289-68-0 cis-1-(Boc)-4-(4-bromo-phenoxy)-L-proline methyl ester 
• 848475-23-0 (2S,4S)-4-(3-Bromo-benzyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 259214-70-5 (2S,4R)-4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 

Relevant articles and documents

Synthesis of tri- and tetrasaccharide glycosides of (4S)-4-hydroxy-d-proline relevant to the cell wall O-glycans of green alga Chlamydomonas reinhardtii

The synthesis of tri- and tetrasaccharide glycosides of (4S)-4-hydroxy-d-proline 1 and 2 with unusual glycan motifs has been achieved efficiently. The assembly of the synthetically challenging 1,2-cis linked arabino- and galactofuranoside frameworks withi

Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates

Alpha-amanitin, an extremely toxic bicyclic octapeptide extracted from the death-cap mushroom, Amanita phalloides, is a highly selective allosteric inhibitor of RNA polymerase II. Following on growing interest in using this toxin as a payload in antibody-drug conjugates, herein we report the synthesis and biochemical evaluation of several new derivatives of this toxin to probe the role of the trans-hydroxyproline (Hyp), which is known to be critical for toxicity. This structure activity relationship (SAR) study represents the first of its kind to use various Hyp-analogs to alter the conformational and H-bonding properties of Hyp in amanitin.

Synthesis process of N-BOC-cis-4-hydroxyproline methyl ester

The invention discloses a synthesis process of N-BOC-cis-4-hydroxyproline methyl ester. The synthesis process comprises the following steps: (1) adding raw materials including dichloromethane, 4-hydroxy-L-proline and DMAP into a 2 L reaction flask, stirring, slowly dropwise adding BOC anhydride into the reaction liquid, after dropwise adding, sampling, carrying out TLC, completely reacting the rawmaterials, adding water into the reaction liquid after treatment, stirring at a temperature of 20-30 DEG C, separating the liquid, drying an organic phase by using anhydrous sodium sulfate, and concentrating under reduced pressure to obtain a white solid product; and (2) taking the obtained product, adding tetrahydrofuran and DCC into a 5 L reaction flask, stirring at 20-30 DEG C to react for 1 hour, dropwise adding methanol into the reaction solution, keeping the temperature after dropwise adding, sampling, carrying out TLC until the reaction is complete, filtering the reaction solution, collecting the filtrate, concentrating under reduced pressure until no liquid flows out to obtain a white solid crude product, heating, collecting the filtrate, collecting a filter cake, and drying the filter cake to obtain a white solid. According to the invention, the product is prepared with high quality and high yield.