213137-33-8

Basic information

• Product Name: 2-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester,(1R,5R,6R)-rel-(9CI)
• Synonyms: 2-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester,(1R,5R,6R)-rel-(9CI)
• CAS NO: 213137-33-8
• Molecular Formula: C8H12O3
• Molecular Weight: 156.17908
• Product Categories: CARBOXYLICESTER
• Mol File: 213137-33-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester,(1R,5R,6R)-rel-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester,(1R,5R,6R)-rel-(9CI)(213137-33-8)
• EPA Substance Registry System: 2-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester,(1R,5R,6R)-rel-(9CI)(213137-33-8)

Safety Data

• Hazardous Substances Data: 213137-33-8(Hazardous Substances Data)

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 104036-66-0 (2-ethoxy-tetrahydro-[3]furyl)-acetic acid ethyl ester 
• 90113-46-5 ethyl 2-(tetrahydrofuran-3-yl)acetate 
• 99418-15-2 2-oxabicyclo[3.1.0]hexane-6-carboxylic acid 

Relevant articles and documents

FUSED TRICYCLIC ETHER CARBAMATES AND THEIR USE

Tricylic ether carbamates that inhibit HIV proteolytic enzymes and processes for preparing the compounds are describes. Methods of using the disclosed compounds for treating patients infected with HIV are also described.

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The annulation reaction between various indoles and 2-alkoxycyclopropanoate esters is reported. Both high efficiency and complete stereochemical control were observed in some cases with this annulation process. A single stereocenter on the cyclopropane controls the diastereoselective formation of up to four new stereocenters. A different reaction course was observed with 3-substituted indole substrates, and an intervening C-3 to C-2-migration process arose that gives synthetically useful C-2 alkylation indole products.

BENZO(5,6)CYCLOHEPTA(1,2-B)PYRIDINE DERIVATIVES USEFUL FOR INHIBITION OF FARNESYL PROTEIN TRANSFERASE

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A Powerful New Strategy for Diversity-Oriented Synthesis of Pyrroles from Donor-Acceptor Cyclopropanes and Nitriles

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Highly Enantioselective Intermolecular Cu(I)-Catalyzed Cyclopropanation of Cyclic Enol Ethers. Asymmetric Total Synthesis of (+)-Quebrachamine

A set of cyclic enol ethers derived from 2,3-dihydrofuran 35 and 3,4-dihydropyran 8 with a varying substitution pattern at the olefinic system were synthesized. Evans's ligand 5 with Cu(I)OTf was found to be an effective catalyst in the cyclopropanation reaction between cyclic enol ethers 14, 19, 28-31, and 33 and ethyl diazoacetate 6 to give diastereoselectivities up to exo/endo = 95:5 and enantioselectivities higher than 95% in nearly all cases. Because of the selective building of a quarternary carbon center and good yields in the formation of bicyclic structures 34c-h, the reaction was used as a key step in the asymmetric synthesis of (+)-quebrachamine 7, an indole alkaloid of the Aspidosperma family. After acid-induced ring opening of bicyclic compound 34f to lactone 40 followed by LiAlH4 reduction to the masked aldehyde 41, a reaction with tryptamine gave intermediate 42. This alcohol was efficiently converted into the indole alkaloid (+)-quebrachamine 7 in an overall yield of 37% starting from the chiral synthon 34f. Moreover it revealed the absolute configuration of the quarternary center of the cyclopropanation product 34f to be S.

Cycloadditions of Diazoalkanes to Enol Ethers Catalyzed by Chromium Complexes - The First Direct Spectroscopic Observation of a Carbene Complex Intermediate

Keywords: carbene complexes; chromium; cyclopropanations; homogeneous catalysis