635319-09-4

Basic information

• Product Name: (3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate
• Synonyms: (3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate;tert-butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS NO: 635319-09-4
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.26216
• Product Categories: Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 635319-09-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 340.3±27.0 °C(Predicted)
• Appearance: /
• Density: 1.190±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 14.49±0.40(Predicted)
• CAS DataBase Reference: (3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate(635319-09-4)
• EPA Substance Registry System: (3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxyMethyl)pyrrolidine-1-carboxylate(635319-09-4)

Safety Data

• Hazardous Substances Data: 635319-09-4(Hazardous Substances Data)

Usage

Uses

(3R,4R)-tert-Butyl 3-Hydroxy-4-(hydroxymethyl)pyrrolidine-1-carboxylate has been used as a reactant for the preparation of transition state analogue inhibitors of human 5’-Methylthioadenosine phosphorylase (MTAP).

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1027-35-6 1-Benzyl-4-oxo-pyrrolidine-3-carboxylic Acid Ethyl Ester 
• 795-18-6 3-(benzyl-ethoxy-carbonylmethyl-amino)-propionic acid ethyl ester 
• 3783-61-7 diethyl 2-azabutane-1,4-dicarboxylate 
• 871086-00-9 (3S,4R)-1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylic acid 
• 71336-69-1 (+/-)-trans-ethyl 1-benzyl-4-hydroxy-5-oxopyrrolidine-3-carboxylate 
• 253129-03-2 (3R, 4R)-1-benzyl-4-(hydroxymethyl)pyrrolidin-3-ol 
• 1523541-94-7 (3S,4R)-1-tert-butyl 3-ethyl 4-hydroxypyrrolidine-1,3-dicarboxylate 
• 849935-77-9 ethyl (3S,4R)-1-benzyl-4-hydroxypyrrolidine-3-carboxylate 
• 267421-93-2 (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine 
• 635319-08-3 (3R,4S)-N-tert-butoxycarbonyl-4-[(1S)-1,2-dihydroxyethyl]-3-hydroxypyrrolidine 

Downstream Products

• 666831-07-8 C₂₅H₄₁NO₆S 
• 1242166-93-3 (3R,4R)-tert-butyl 4-(benzoyloxymethyl)-3-(tert-butyldimethylsilyloxy)pyrrolidine-1-carboxylate 
• 1011300-20-1 (3R,4R)-tert-butyl 4-(benzoyloxymethyl)-3-hydroxypyrrolidine-1-carboxylate 
• 267421-93-2 (3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidine 
• 635319-16-3 (3R,4R)-1-{[6-O-benzyl-7-benzyloxymethyl-9-deaza-2-bis(4-methoxybenzyl)guanin-9-yl]methyl}-3-hydroxy-4-hydroxymethylpyrrolidine 
• 635319-15-2 7-(3-benzyloxy-4-benzyloxymethyl-pyrrolidin-1-ylmethyl)-5-benzyloxymethyl-4-tert-butoxy-5H-pyrrolo[3,2-d]pyrimidine 
• 666830-86-0 (3R,4R)-1-[(7-benzyloxymethyl-9-deazahypoxanthin-9-yl)methyl]-3-benzyloxy-4-benzyloxymethylpyrrolidine 
• 705060-10-2 (3R,4R)-3-[(3-acetoxy-4-acetoxymethylpyrrolidin-1-yl)methyl]benzamide 
• 705060-19-1 (3R,4R)-3-[(3-hydroxy-4-methanesulfonylmethylpyrrolidin-1-yl)methyl]benzamide 
• 705060-14-6 (3R,4R)-3-[(3-hydroxy-4-hydroxymethylpyrrolidin-1-yl)methyl]benzamide 
• 666831-21-6 (3R,4S)-3-acetoxy-1-[(7-benzyloxymethyl-6-tert-butoxy-9-dezahypoxanthin-9-yl)methyl]-4-benzylthiomethylpyrrolidine 
• 666831-20-5 (3R,4S)-1-[(7-benzyloxymethyl-9-dezapurin-9-yl)methyl]-4-benzylthiomethyl-3-hydroxypyrrolidine 

Relevant articles and documents

An aza-nucleoside, fragment-like inhibitor of the DNA repair enzyme alkyladenine glycosylase (AAG)

The DNA repair enzyme AAG has been shown in mice to promote tissue necrosis in response to ischaemic reperfusion or treatment with alkylating agents. A chemical probe inhibitor is required for investigations of the biological mechanism causing this phenomenon and as a lead for drugs that are potentially protective against tissue damage from organ failure and transplantation, and alkylative chemotherapy. Herein, we describe the rationale behind the choice of arylmethylpyrrolidines as appropriate aza-nucleoside mimics for an inhibitor followed by their synthesis and the first use of a microplate-based assay for quantification of their inhibition of AAG. We finally report the discovery of an imidazol-4-ylmethylpyrrolidine as a fragment-sized, weak inhibitor of AAG.

SALT AND POLYMORPHIC FORMS OF (3R,4S)-L-((4-AMINO-5H-PYRROLO[3,2-D]PYRIMIDIN-7-YL)METHYL)-4(METHYLTHIOMETHYL)PYRODIN-3-OL(MTDIA)

The invention relates to salt forms of (3R,4S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-4-(methylthiomethyl)pyrrolidin-3-ol, as well as polymorphic forms of the salts. The invention further relates to processes for preparing the salt forms and to the use of the salt forms in the treatment of diseases and disorders where it is desirable to inhibit 5'-methylthioadenosine phosphorylase (MTAP).

A practical synthesis of (3R,4R)-N-tert-butoxycarbonyl-4- hydroxymethylpyrrolidin-3-ol

The title compound (+)-5, required for production of transition state analogue inhibitors of enzymes involved in T-cell-dependent disorders, was synthesized in five steps. A 1,3-dipolar cycloaddition of the nitrone formed from formaldehyde and N-benzylhydroxylamine to diethyl maleate gave the racemic cis-isoxazolidine (±)-7. Reduction of the N-O bond of this compound gave pyrrolidone (±)-8 in excellent yield. A very efficient enzymic resolution of this racemic product led to the title enantiomer (+)-5. This route employs only one chromatographic purification. The Royal Society of Chemistry.