137365-16-3

Basic information

• Product Name: (+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-D-THREITOL
• Synonyms: (4S,5S)-2,2-dimethyl-α4,α4,α5,α5-tetra-2-naphthalenyl-1,3-Dioxolane-4,5-dimethanol;(+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-D-THREITOL;(4S-TRANS)-2,2-DIMETHYL-ALPHA,ALPHA,ALPHA',ALPHA'-TETRA(2-NAPHTHYL)-1,3-DIOXOLANE-4,5-DIMETHANOL;(4S,5S)-2,2-DIMETHYL-ALPHA,ALPHA,ALPHA',ALPHA'-TETRA(2-NAPHTHYL)DIOXOLANE-4,5-DIMETHANOL;(+)-DINOL;(+)-2,3-O-isopropylidene-1,1,4,4-tetra (2-naph.)-D-threitol;(4S-trans)-2,2-di-me-A,A,A,A-tetra-2-nap -dioxo;(4S-TRANS)-2,2-DI-ME-A,A,A',A'-TETRA-2-N AP -DIOXOLAN-DIMETHANOL, 98%(99% EE/HPLC
• CAS NO: 137365-16-3
• Molecular Formula: C47H38O4
• Molecular Weight: 666.8
• Mol File: 137365-16-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 214-216 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.269g/cm³
• Refractive Index: 1.718
• Storage Temp.: 2-8°C
• PKA: 12.14±0.29(Predicted)
• CAS DataBase Reference: (+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-D-THREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-D-THREITOL(137365-16-3)
• EPA Substance Registry System: (+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-D-THREITOL(137365-16-3)

Safety Data

• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 137365-16-3(Hazardous Substances Data)

Usage

Uses

Reagent for the highly enantioselective addition of primary alkyl Grignards to ketones. Chiral auxiliary used for the asymmetric addition of nucleophiles to carbonyls.

InChI:InChI=1/C47H38O4/c1-45(2)50-43(46(48,39-23-19-31-11-3-7-15-35(31)27-39)40-24-20-32-12-4-8-16-36(32)28-40)44(51-45)47(49,41-25-21-33-13-5-9-17-37(33)29-41)42-26-22-34-14-6-10-18-38(34)30-42/h3-30,43-44,48-49H,1-2H3/t43-,44-/m0/s1

Upstream product

• 580-13-2 2-bromonaphthalene 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 73346-73-3 (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 37031-29-1 (+)-dimethyl-2,3-O-isopropylidene-D-tartrate 
• 1236286-39-7 C₁₄H₁₆N₂*C₄₇H₃₈O₄ 

Downstream Products

• 1236286-39-7 C₁₄H₁₆N₂*C₄₇H₃₈O₄ 

Relevant articles and documents

Phosphite-Catalyzed C?H Allylation of Azaarenes via an Enantioselective [2,3]-Aza-Wittig Rearrangement

A phosphite-mediated [2,3]-aza-Wittig rearrangement has been developed for the regio- and enantioselective allylic alkylation of six-membered heteroaromatic compounds (azaarenes). The nucleophilic phosphite adducts of N-allyl salts undergo a stereoselective base-mediated aza-Wittig rearrangement and dissociation of the chiral phosphite for overall C?H functionalization of azaarenes. This method provides efficient access to tertiary and quaternary chiral centers in isoquinoline, quinoline, and pyridine systems, tolerating a broad variety of substituents on both the allyl part and azaarenes. Catalysis with chiral phosphites is also demonstrated with synthetically useful yields and enantioselectivities.

Enantioselective Ni-Al Bimetallic Catalyzed exo -Selective C-H Cyclization of Imidazoles with Alkenes

A Ni-Al bimetallic catalyzed enantioselective C-H exo-selective cyclization of imidazoles with alkenes has been developed. A series of bi- or polycyclic imidazoles with β-stereocenter were obtained in up to 98% yield and >99% ee. The bifunctional SPO ligand-promoted bimetallic catalysis proved to be critical to this challenging stereocontrol.

A quaternary phosphonium salt compound and its preparation method

The present invention discloses a quaternary phosphonium salt compound and a preparation method thereof. The method uses cheap and readily available L-tartaric acid as the raw material, and conducts carboxyl esterification, hydroxyl protection, Grignard reaction, azide substitution, azide reduction and final reaction with phosphorus pentachloride, so as to obtain the quaternary phosphonium salt compound. The quaternary phosphonium salt compound is a novel Bronsted acid catalyst (a hydrogen bond donor catalyst), and can be used in the catalysis of asymmetric Mannich reaction, Michael reaction and Henry reaction.