87248-50-8

Basic information

• Product Name: (+)-NOE'S REAGENT
• Synonyms: (2R,3AS,4R,7AS)-OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN-2-YL ETHER;(+)-MBF-OH DIMER;BIS[(2R,3AS,4R,7AS)-OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN-2-YL] ETHER;(+)-NOE-LACTOL(R) DIMER;(+)-NOE'S REAGENT;(+)-NOE-LACTOL DIMER, 99+%;BIS[(2R,3AS,4R,7AS)-OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN-2-YL] ETHER [FOR OPTICAL RESOLUTION] 98+%;Bis[(2R,3aS,4R,7aS)-octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl] Ether [for Optical Resolution]
• CAS NO: 87248-50-8
• Molecular Formula: C₂₄H₃₈O₃
• Molecular Weight: 374.56
• Product Categories: for Resolution of Alcohols & Thiols;Optical Resolution;Synthetic Organic Chemistry
• Mol File: 87248-50-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 149-151 °C
• Boiling Point: 435.884oC at 760 mmHg
• Flash Point: 148.712oC
• Appearance: /
• Density: 1.12g/cm3
• Refractive Index: 202.5 ° (C=2, THF)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-NOE'S REAGENT(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-NOE'S REAGENT(87248-50-8)
• EPA Substance Registry System: (+)-NOE'S REAGENT(87248-50-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 87248-50-8(Hazardous Substances Data)

Usage

Uses

(+)-Noe-lactol? dimer can be used to prepare:Axially chiral isoquinoline derivatives by reacting with pyridinium?p-toluenesulfonate.Halofuginone lactate.

Upstream product

• 81925-09-9 (1S,2R,4R,6R,7S)-1,10,10-Trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]decan-4-ol 
• 81969-33-7 (3aR-(3aα,4β,7β,7aα))-3a,4,5,6,7,7a-Hexahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2(3H)-on 
• 108031-75-0 (1S,2R,4R,6R,7S)-1,10,10-Trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]decan-4-ol 
• 108031-76-1 <2R-(2α,3aα,4β,7β,7aα)>-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-ol 
• 81925-09-9 <2S-(2α,3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-ol 
• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 67-56-1 methanol 
• 82009-52-7 <2R-(2α(R*),3aα,4α,7α,7aα)>-α-<(2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>benzolacetonitril 
• 81978-47-4 <2R-(2α(S*),3aα,4α,7α,7aα)>-α-<(2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>benzolacetonitril 

Downstream Products

• 100680-93-1 <2R-<2α(αR^*,βS^*),3aα,4α,7α,7aα>>-β-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-α-phenylbenzolethanol 
• 100680-94-2 <2R-<2α(αS^*,βR^*),3aα,4α,7α,7aα>>-β-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-α-phenylbenzolethanol 
• 100680-95-3 <2R-<2α(R^*),3aα,4α,7α,7aα>>-2-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-1,2-diphenylethanon 
• 100596-90-5 <2R-<2α(S^*),3aα,4α,7α,7aα>>-2-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-1,2-diphenylethanon 
• 81978-48-5 <2R-(2α(R*),3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-2-<(1-phenylethyl)thio>-4,7-methanobenzofuran 
• 82009-53-8 <2R-(2α(S*),3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-2-<(1-phenylethyl)thio>-4,7-methanobenzofuran 
• 81978-48-5 (1R,2S,4S,6S,7R)-1,10,10-Trimethyl-4-((R)-1-phenyl-ethylsulfanyl)-3-oxa-tricyclo[5.2.1.0^2,6]decane 
• 81978-48-5 (1R,2S,4S,6S,7R)-1,10,10-Trimethyl-4-((S)-1-phenyl-ethylsulfanyl)-3-oxa-tricyclo[5.2.1.0^2,6]decane 
• 105961-40-8 <2S-(2α(S^*),3aα,4α,7α,7aα)>-7,8,8-Trimethyl-2-(1,2-diphenylethoxy)-octahydro-4,7-methano-1-benzofuran 
• 106033-50-5 (1R,2S,4S,6S,7R)-4-((S)-1,2-Diphenyl-ethoxy)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]decane 
• 81925-14-6 <2R-(2α,3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-2-(1,1-diphenylmethoxy)-7,8,8-trimethyl-4,7-methanobenzofuran 
• 81925-14-6 (1R,2S,4S,6S,7R)-4-Benzhydryloxy-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]decane 
• 81978-44-1 <2S-(2α(S*),3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-2-(1-phenylethoxy)-4,7-methanobenzofuran 
• 82009-49-2 <2S-(2α(R*),3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-2-(1-phenylethoxy)-4,7-methanobenzofuran 

Relevant articles and documents

Stereoelektronische Effekte und chirale Erkennung: Ein natuerliches Verwandtschaftssystem chiraler Verbindungen basierend auf Selektivitaeten bei der Acetalbildung

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Chiral Lactols, II. Racemate Separation and Enantioselective Acetalisation with the 2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl Protective Group

A simple method for the resolution of the chiral alcohols, cyanohydrins, thiols and amines rac-2a - f by the reaction with the chiral protective group 1a ( or 1b, respectively) is described.The diastereomeric derivatives 3a - f and 4a - f are separated by column chromatography or crystallisation.Subsequent methanolysis or hydrolysis, respectively, yields the enantiomers and the recovered protective group.With rac-2a - c preferential acetalisation of the (R)-enantiomers was observed.This phenomenon was investigated by modification of the protective group.Considerations on conformations of 3a point to an important role of the anomeric and exo-anomeric effect in this enantioselective reaction.