86728-74-7

Basic information

• Product Name: tetrahydro-2H-pyran-2,3-diol
• Synonyms: tetrahydro-2H-pyran-2,3-diol;Einecs 289-277-9
• CAS NO: 86728-74-7
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.1311
• EINECS: 289-277-9
• Mol File: 86728-74-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 224.6°Cat760mmHg
• Flash Point: 89.6°C
• Appearance: /
• Density: 1.291g/cm³
• Vapor Pressure: 0.0181mmHg at 25°C
• Refractive Index: 1.52
• CAS DataBase Reference: tetrahydro-2H-pyran-2,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: tetrahydro-2H-pyran-2,3-diol(86728-74-7)
• EPA Substance Registry System: tetrahydro-2H-pyran-2,3-diol(86728-74-7)

Safety Data

• Hazardous Substances Data: 86728-74-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H10O3/c6-4-2-1-3-8-5(4)7/h4-7H,1-3H2

Upstream product

• 1003-57-2 trans-3-chloro-2-hydroxytetrahydropyran 
• 343228-09-1 Trifluoro-acetic acid 3-(2,2,2-trifluoro-acetoxy)-tetrahydro-pyran-2-yl ester 
• 110-87-2 3,4-dihydro-2H-pyran 
• 1262029-69-5 N-(tert-butoxycarbonyl)-L-phenylalanine 4'-acetoxy-1'-formyl-butyl ester 
• 1262029-70-8 N-(tert-butoxycarbonyl)-L-tyrosine 4'-acetoxy-1'-formyl-butyl ester 
• 1230-36-0 bis-(3-acetoxy-tetrahydro-pyran-2-yl)-ether 

Downstream Products

• 100128-06-1 tetrahydro-furan-2-carbaldehyde-(4-nitro-phenylhydrazone) 
• 1204-56-4 diacetoxy-2,3 tetrahydropyranne 
• 106269-94-7 5-hydroxy-1-p-toluidino-pentan-2-one 
• 6559-02-0 trans-3-hydroxy-2-methoxytetrahydropyran 
• 6559-11-1 cis-3-Hydroxy-2-methoxytetrahydropyran 
• 124502-72-3 2-(benzyloxy)tetrahydro-2H-pyran-3-ol 
• 97102-46-0 (2S,4aR,8aS)-2-Phenylsulfanyl-octahydro-pyrano[3,2-b]pyran 
• 97102-46-0 (2R,4aR,8aS)-2-Phenylsulfanyl-octahydro-pyrano[3,2-b]pyran 
• 97102-69-7 3-[(2R,3S)-3-(Tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-propan-1-ol 
• 97102-68-6 3-[(2S,3S)-3-(Tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-propan-1-ol 

Relevant articles and documents

Stereoselective template-directed C-glycosidation. Synthesis of 5-membered oxygen heterocycles via cation-mediated intramolecular cyclization reactions

Construction of 5-membered oxygen heterocycles by intramolecular template- directed C-glycosidation is described. Alkylation of thioglycoside 5 with enone 6 followed by enol etherification gave cyclization substrates 8. Compound 8a underwent silver(I) trifluoromethanesulfonate-mediated ring- closure to give a 1.7:1 mixture of 9α and 9β; isomer 8s gave an 8.5:1 ratio. Some derivatization reactions of the bicyclic products are described.

Arylboronic acid-mediated glycosylation of 1,2-dihydroxyglucoses

- We explored direct dehydrative coupling of tetrahydro-2H-pyran-2,3-diol or a 1,2-dihydroxy sugar with various alcohols using a range of arylboronic acids. Among the catalysts, 2-borono-4-trifluoromethylbenzoic acid efficiently promoted acetalization of tetrahydro-2H-pyran-2,3-diol. Ferroceniumboronic acid showed the best catalytic activity for glycosylation of the 1,2-dihydroxy sugar. The major products were 1,2-cJi-a-D-glucopyranosides.

Template-directed intramolecular C-glycosidation. Formation of tetrahydrofurans and application to the synthesis of a higher-order sugar

Cation-mediated cyclisation reactions of silyl enol ether-containing thioglycosides give bicyclic ketotetrahydrofurans. Cyclisation of an analogous 3-phenyl-2-propenyl ether-containing substrate gives an intermediate in the total synthesis of the higher-order sugar 2,3-dideoxy-D- manno-2-octulopyranosonic acid.