61478-26-0

Basic information

• Product Name: BOC-HYP-OL
• Synonyms: TERT-BUTYL (2S,4R)-4-HYDROXY-2-(HYDROXYMETHYL)PYRROLIDINE-1-CARBOXYLATE;(-)-N-BOC-L-4-HYDROXYPROLINOL;N-BOC-TRANS-4-HYDROXY-L-PROLINOL;N-T-BUTOXYCARBONYL-TRANS-4-HYDROXY-L-PROLINOL;BOC-HYP-OL;BOC-PRO(4-HYDROXY)-OL;BOC-TRANS-4-HYDROXY-L-PROLINOL;1-Pyrrolidinecarboxylic acid, 4-hydroxy-2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (2S,4R)-
• CAS NO: 61478-26-0
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.26
• Product Categories: Amino Acid Derivatives;Amino Alcohols;Peptide Synthesis
• Mol File: 61478-26-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 81-86 °C(lit.)
• Boiling Point: 340.296 °C at 760 mmHg
• Flash Point: 159.605 °C
• Appearance: /
• Density: 1.19 g/cm³
• Refractive Index: 1.511
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.57±0.40(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: BOC-HYP-OL(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-HYP-OL(61478-26-0)
• EPA Substance Registry System: BOC-HYP-OL(61478-26-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 61478-26-0(Hazardous Substances Data)

Usage

Uses

BOC-HYP-OL is a useful reactant used in the preparation of 4-purinylpyrrolidine nucleosides, kinase inhibitors and antibacterial agents.

InChI:InChI=1/C10H19NO4/c1-10(2,3)15-9(14)11-5-8(13)4-7(11)6-12/h7-8,12-13H,4-6H2,1-3H3/t7-,8+/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 1315590-90-9 tert-butyl (2S,4R)-4-methoxy-2-((trityloxy)methyl)pyrrolidine-1-carboxylate 
• 132666-68-3 (1S,4S)-5-Benzyl-2-tert-butoxycarbonyl-2,5-diazabicyclo<2.2.1>heptane 

Relevant articles and documents

OLIGONUCLEOTIDE-LIGAND CONJUGATES AND PROCESS FOR THEIR PREPARATION

The present invention relates to ligand conjugates of oligonucleotides (e.g., iRNA agents) and methods for their preparation. The ligands are derived primarily from monosaccharides These conjugates are useful for the in vivo delivery of oligonucleotides.

A practical synthesis of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane

The rigid piperazine homologue 2,5-diazabicyclo[2.2.1]heptane (DBH) finds extensive application in medicinal chemistry and pharmaceutical research, but access to this scaffold is non-trivial. This letter details a concise synthetic sequence that gives ready access to DBH on gram scale. The route features a Staudinger reduction of an azide to facilitate a transannular cyclisation.

Synthesis of (1S,4S)-2-Thia-5-azabicycloheptane

Starting from trans-4-hydroxy-L-proline, (1S,4S)-2-thia-5-azabicycloheptane (1) has been synthesised via the key intermediate N-(t-butoxycarbonyl)-trans-4-hydroxy-L-prolinol ditosylate (7).