109789-17-5

Basic information

• Product Name: cis-Hexahydro-3-methylene-furo[2,3-b]furan
• Synonyms: (+/-)-Hexahydro-3-methylene-cis-furo[2,3-b]furan;cis-Hexahydro-3-methylene-furo[2,3-b]furan
• CAS NO: 109789-17-5
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• Product Categories: Chiral Reagents;Heterocycles;Intermediates;Chiral Reagents, Heterocycles, Intermediates
• Mol File: 109789-17-5.mol

Chemical Properties

• Boiling Point: 172.711°C at 760 mmHg
• Flash Point: 50.643°C
• Appearance: /
• Density: 1.089g/cm³
• Vapor Pressure: 1.753mmHg at 25°C
• Refractive Index: 1.487
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: cis-Hexahydro-3-methylene-furo[2,3-b]furan(CAS DataBase Reference)
• NIST Chemistry Reference: cis-Hexahydro-3-methylene-furo[2,3-b]furan(109789-17-5)
• EPA Substance Registry System: cis-Hexahydro-3-methylene-furo[2,3-b]furan(109789-17-5)

Safety Data

• Hazardous Substances Data: 109789-17-5(Hazardous Substances Data)

Usage

Chemical Properties

Pale-Yellow Oil

Uses

P2-ligands for HIV-1 protease inhibitors.

InChI:InChI=1/C7H10O2/c1-5-4-9-7-6(5)2-3-8-7/h6-7H,1-4H2/t6-,7+/m1/s1

Upstream product

• 445389-46-8 3-bromo-2-(2-propyn-1-yloxy)tetrahydrofuran 
• 109789-15-3 (2RS,3RS)-3-bromo-2-(prop-2-yn-1-yloxy)-tetrahydrofuran 

Downstream Products

• 1256492-73-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-d1 4-nitrophenylcarbonate 
• 109789-20-0 Toluene-4-sulfonic acid (3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester 
• 156879-13-9 L-739,594 
• 156879-13-9 L-739-594 
• 156928-09-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 
• 156928-10-8 (3S,3aR,6aS)-3-hydroxyhexahydrofuro<2,3-b>furan 
• 53616-34-5 2-(furan-3-yl)ethan-1-ol 
• 109789-18-6 (2aRS,3aSR)-hexahydrofuro[2,3-b]furan-3-one 

Relevant articles and documents

SINTHESIS AND OPTICAL RESOLUTION OF HIGH AFFINITY P2-LIGANDS FOR HIV-1 PROTEASE INHIBITORS

Racemic bis-tetrahydrofuran ligand 6 was efficiently synthesized utilizing catalytic cobaloxime 10 mediated radical cyclization as the key step.Optical resolution of the racemic alcohol with immobilized-Amano lipase, afforded optically pure ligands.

CHEMICAL COMPOUNDS

The present invention relates to highly functionalized 1,3-diamino-propan-2-ols and pharmaceutically acceptable salts thereof. More specifically, the invention relates to highly functionalized 1,3-diamino-propan-2-ols that are derivatives of the HIV prote

Towards aflatoxins: a formal synthesis of aflatoxin B2

The development of a formal synthesis of aflatoxin B2 is described, which utilizes a D?tz benzannulation reaction as a key step.

FITNESS ASSAY AND ASSOCIATED METHODS

The present invention provides an assay for determining the biochemical fitness of a biochemical species in a mutant replicating biological entity relative to its predecessor. The present invention further provides a continuous fluorogenic assay for measuring the anti-HIV protease activity of protease inhibitor. The present invention also provides a method of administering a therapeutic compound that reduces the chances of the emergence of drug resistance in therapy. The present invention also provides a compound of formula (I) or a pharmaceutically acceptable salt, a prodrug, a composition, or an ester thereof, wherein A is a group of formulas (A), (B), (C) or (D); R1, R2, R3, R5 or R6 is H, or an optionally substituted and/or heteroatom-bearing alkyl, alkenyl, alkynyl, or cyclic group; Y and/or Z are CH2, O, S, SO, SO2, amino, amides, carbamates, ureas, or thiocarbonyl derivatives thereof, optionally substituted with an alkyl, alkenyl, or alkynyl group; n is from 1 to 5; X is a bond, an optionally substituted methylene or ethylene, an amino, O or S; Q is C(O), C(S), or SO2; m is from 0 to 6; R4 is OH, ═O (keto), NH2, or alkylamino, including esters, amides, and salts thereof; and W is C(O), C(S), S(O), or SO2. Optionally, R5 and R6, together with the N—W bond of formula (I), comprise a macrocyclic ring.

A formal synthesis of aflatoxin B2: a Doetz benzannulation approach

A Doetz benzannulation reaction has been utilized in the synthesis of the furo[2,3-b]furan core of aflatoxin B2.

Nonpeptidal P2 ligands for HIV protease inhibitors: structure-based design, synthesis, and biological evaluation.

Design and synthesis of nonpeptidal bis-tetrahydrofuran ligands based upon the X-ray crystal structure of the HIV-1 protease-inhibitor complex 1 led to replacement of two amide bonds and a 10 pi-aromatic system of Ro 31-8959 class of HIV protease inhibitors. Detailed structure-activity studies have now established that the position of ring oxygens, ring size, and stereochemistry are all crucial to potency. Of particular interest, compound 49 with (3S,3aS,6aS)-bis-Thf is the most potent inhibitor (IC50 value 1.8 +/- 0.2 nM; CIC95 value 46 +/- 4 nM) in this series. The X-ray structure of protein-inhibitor complex 49 has provided insight into the ligand-binding site interactions. As it turned out, both oxygens in the bis-Thf ligands are involved in hydrogen-bonding interactions with Asp 29 and Asp 30 NH present in the S2 subsite of HIV-1 protease. Stereoselective routes have been developed to obtain these novel ligands in optically pure form.

A NEW ROUTE TO PERHYDRO- AND TETRAHYDRO- FURO-2,3b FURANS VIA RADICAL CYCLISATION

Perhydrofuro-2,3b furans have been prepared in high yield by radical cyclisation of unsaturated bromo acetals.Their transformation into tetrahydro derivatives is described along with a radical anneltion to 2,3- dihydrofurans by tributyltin iodoacetate.