27304-20-7

Basic information

• Product Name: 2 3-O-CYCLOHEXYLIDENE-D-RIBONIC ACID
• Synonyms: 2 3-O-CYCLOHEXYLIDENE-D-RIBONIC ACID;2,3-CYCLOHEXYLIDENE-D-RIBONIC ACID GAMMA;2,3-cyclohexylidene-d-ribonic acid γ-lactone;D-Ribonolactone 2,3-Cyclohexyl Ketal;2,3-O-Cyclohexylidene-D-ribonic Acid γ-lactone;2,3-O-Cyclohexylidene-D-ribono-1,4-lactone
• CAS NO: 27304-20-7
• Molecular Formula: C₁₁H₁₆O₅
• Molecular Weight: 246.25702
• Product Categories: Carbohydrates & Derivatives;Intermediates
• Mol File: 27304-20-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 130-133 °C(lit.)
• Boiling Point: 424.5±40.0 °C(Predicted)
• Appearance: /
• Density: 1.34±0.1 g/cm3(Predicted)
• Solubility: Chloroform, Dichloromethane,
• PKA: 13.68±0.10(Predicted)
• CAS DataBase Reference: 2 3-O-CYCLOHEXYLIDENE-D-RIBONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2 3-O-CYCLOHEXYLIDENE-D-RIBONIC ACID(27304-20-7)
• EPA Substance Registry System: 2 3-O-CYCLOHEXYLIDENE-D-RIBONIC ACID(27304-20-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 27304-20-7(Hazardous Substances Data)

Usage

Chemical Properties

Pale Solid

Uses

Protected D-Ribonolactone.

Upstream product

• 931-57-7 1-methoxy-cyclohex-1-ene 
• 5336-08-3 D-Ribono-1,4-lactone 
• 123168-27-4 2,3-O-cyclohexylidene-D-ribofuranose 
• 108-94-1 cyclohexanone 
• 27304-21-8 3,4-O-cyclohexylidene-L-ribonic acid δ-lactone 
• 546141-19-9 2,3-O-cyclohexylidene-D-ribonolactone 
• 532-20-7 D-Ribose 

Downstream Products

• 186803-48-5 2,3-O-cyclohexylidene-L-(-)-erythruronic acid 
• 28277-83-0 2,3-O-Cyclohexylidene-5-O-p-toluenesulfonyl-D-ribono-1,4-lactone 
• 111005-65-3 (-)-2,3-(cyclohexylidenedioxy)-4-cyclopentenone 
• 186790-80-7 2,3-(cyclohexylidenedioxy)-4-hydroxy-4-(2-propyloxy)butanoic acid lactone 
• 129390-48-3 N-cyclohexyl-(3R,4S,5R)-3,4-(cyclohexylidenedioxy)-5-hydroxy-2-pyrolidinone 
• 129390-43-8 N-benzyl-(3R,4S,5R)-3,4-(cyclohexylidenedioxy)-5-hydroxy-2-pyrolidinone 
• 129390-47-2 (2R,3R)-3-((R)-1,2-Dihydroxy-ethyl)-1,4-dioxa-spiro[4.5]decane-2-carboxylic acid benzylamide 
• 120666-63-9 N-(2R)-(2-phenyl-1-hydroxyethyl)-(3R,4S,5R)-3,4-(cyclohexylidenedioxy)-5-hydroxy-2-pyrrolidinone 
• 120666-65-1 N-(2R)-<2-phenyl-1-(tert-butyldimethylsiloxy)ethyl>-(3R,4S,5R)-3,4-(cyclohexylidenedioxy)-5-hydroxy-2-pyrrolidinone 
• 129390-49-4 (2R,3R)-3-((R)-1,2-Dihydroxy-ethyl)-1,4-dioxa-spiro[4.5]decane-2-carboxylic acid [(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-amide 

Relevant articles and documents

Synthesis of the tetrahydrofuran unit of varitriol and γ- butyrolactones from 5-oxabicyclo[2.1.1]hexane derivative via oxidative cleavage reactions

A formal synthesis of marine-derived antitumor natural product varitriol from a 5-oxabicyclo[2.1.1]hexane derivative is described. A tetrahydrofuran unit of varitriol embedded with four contiguous stereocenters was synthesized with an overall yield of 10.2% in 11 steps from an oxa-bicyclic system. An unprecedented oxidative cleavage reaction involving scissoring of two CC bonds at oxa-quaternary carbon of THFs leading to γ-butyrolactones was reported and a plausible mechanism has been proposed.

Organotransition Metal Modified Sugars, Part 10. Chromium Iminoglycosylidenes: Synthesis and Application to Photoinduced C-Glycosidation

The iminoglycosylidene complexes 3a,b, 9, and 16a,b are conveniently prepared from the sugar lactams 2a,b, 8, and 15a,b by reaction with K2Cr(CO)5 and subsequent deoxygenation with trimethylsilyl chloride (TMSCl). The Cr(CO)5-stabilized carbene moiety of the imino-D-ribo-pyranosylidene complexes 9 and 16a,b has been exploited in the photoinduced generation of ketene-like species on irradiation with UV light. These intermediates were trapped with methanol to produce the methyl 2,6-imino-D-allonates 10 and 17a,b. The C-glycosidation is β-selective and has been applied futher to the preparation of the galactosyl 2,6-imino-D-allonate 19. Solvent effects suggest that the diastereoselectivity originates in the chromium fragment, which shields the re face of the proposed ketene intermediate. - Keywords: chromium; carbene complexes; glycosides; iminosugars; photolysis

A new synthesis of D-ribonolactone from D-ribose by pyridinium chlorochromate oxidation

2,3-O-Cyclohexylidene-D-ribonolactone is prepared directly from 2,3-O-cyclohexylidene-D-ribose by pyridinium chlorochromate (PCC) oxidation in 55-60% yield.