53951-42-1

Basic information

• Product Name: Tetrahydro-2-methyl-2H-pyran-3,4-diol
• Synonyms: Tetrahydro-2-methyl-2H-pyran-3,4-diol
• CAS NO: 53951-42-1
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• Mol File: 53951-42-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Tetrahydro-2-methyl-2H-pyran-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydro-2-methyl-2H-pyran-3,4-diol(53951-42-1)
• EPA Substance Registry System: Tetrahydro-2-methyl-2H-pyran-3,4-diol(53951-42-1)

Safety Data

• Hazardous Substances Data: 53951-42-1(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 13035-13-7 4,6-O-benzylidene-1,2-dideoxy-D-glucose 
• 55230-27-8 cis-2-methyl-3,4-epoxytetrahydropyran 
• 55230-27-8 trans-2-methyl-3,4-epoxytetrahydropyran 
• 504-60-9 penta-1,3-diene 
• 55230-25-6 6-methyl-3,6-dihydro-2H-pyran 
• 55254-31-4 2-methyl-3,4-epoxytetrahydropyran 
• 2873-29-2 D-glucal triacetate 
• 13035-12-6 3,4,6-tri-O-acetyl-1,2-dideoxy-D-glucopyranose 
• 7103-29-9 1,2-dideoxy-D-allose 
• 3971-47-9 (3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran 
• 720698-25-9 6-O-(4-toluenesulfonyl)-1,2-dideoxy-D-allose 

Downstream Products

• 38877-21-3 2,3-dihydro-5-hydroxy-6-methyl-4H-pyran-4-one 
• 89444-20-2 C₂₀H₁₈N₂O₉ 
• 89444-21-3 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2R,3R,4R)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl ester 
• 89444-21-3 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2S,3S,4S)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

A PYRAN-TYPE GLYCOSIDE FROM DIANTHUS SUPERBUS VAR. LONGICALYCINUS

From the young fresh leaves of Dianthus superbus var. longicalycinus 2-methyl 3,4-dihydroxydihydropyran and its monoglucoside have been isolated.Key Word Index - Dianthus superbus var. longicalycinus; Caryophyllaceae; young leaves; dihydropyrans; 2-methyl-3,4-dihydroxydihydropyran; 2-methyl-3,4-dihydroxydihydropyran-4-O-β-D-glucoside.

Identifying specific conformations by using a carbohydrate scaffold: Discovery of subtype-selective LPA-receptor agonists and an antagonist

Stable and potent subtype-selective lysophosphatidic acid (LPA) analogues (agonists and an antagonist) were developed by using carbohydrates as a core structure (see scheme). An array of molecules with the recognition motifs of LPA (a phosphate anion, an oleoyl group, and a hydrogen-bond acceptor) attached to carbohydrate isomers in different three-dimensional arrangements were tested for LPA-receptor activation or inhibition. R = alkyl.

Acid-catalyzed and Enzymatic Hydrolysis of trans- and cis-2-Methyl-3,4-epoxytetrahydropyran

Whereas the acid-catalyzed hydrolysis of trans- and cis-3,4-epoxy-2-methyltetrahydropyran gives the corresponding diols by opening both at C-4 and C-3 (64percent attack at C-4 in the trans-epoxide, 86percent in the cis-epoxide), the hydrolysis of the same substrates catalyzed by rabbit liver microsomal epoxide hydrolase is entirely regiospecific and involves in both cases exclusive attack at C-4.The racemic cis-epoxide reacts at a faster rate than the trans.The 2R,3R,4S-enantiomer of the latter epoxide reacts at a much faster rate than its antipode to yield the (-)-(2R,3R,4R)-diol which is isolated at least 98 percent optically pure up to almost 50 percent conversion when starting from the racemic substrate.A reference sample of optically pure (+)-(2S,3S,4S)-diol was prepared from L-rhamnose.The enantiomeric excess of the (-)-(2R,3R,4R)-diol was also determined more precisely through g.l.c. analysis of diastereoisomeric MTPA esters.The present results confirm previous hypotheses on the topology of the hydrolase active site and emphasize the overriding importance of the orientation of a lipophilic substituent near the oxirane ring.