3749-36-8

Basic information

• Product Name: 3,4-Dihydro-2H-pyran-2-methanol
• Synonyms: DHP LINKER;2H-PYRAN-2-METHANOL, 3,4-DIHYDRO-;2-HYDROXYMETHYL-3,4-DIHYDRO-2H-PYRAN;3,4-DIHYDRO-2H-PYRAN-2-METHANOL;3,4-DIHYDRO-2H-PYRAN-2-YLMETHANOL;3,4-DIHYDRO-2H-PYRANE-2-METHANOL;3,4-Dihydroxy-2H-pyran-2-Methanol;2-HYDROXYMETHYL-3,4-DIHYDRO-2H-PRYAN(DHP-LINKER)
• CAS NO: 3749-36-8
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• EINECS: 250-545-5
• Product Categories: Miscellaneous;Alkohols;Linkers for Solid Phase Synthesis;Linkers for solid phase synthesis
• Mol File: 3749-36-8.mol

Chemical Properties

• Boiling Point: 92-93 °C25 mm Hg(lit.)
• Flash Point: 85°C
• Appearance: /
• Density: 1.101 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0697mmHg at 25°C
• Refractive Index: n20/D 1.478(lit.)
• Storage Temp.: 2-8°C
• PKA: 14.34±0.10(Predicted)
• BRN: 107275
• CAS DataBase Reference: 3,4-Dihydro-2H-pyran-2-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dihydro-2H-pyran-2-methanol(3749-36-8)
• EPA Substance Registry System: 3,4-Dihydro-2H-pyran-2-methanol(3749-36-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 3749-36-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3,4-Dihydro-2H-pyran-2-methanol is used as a protecting group for alcohols in organic synthesis. It provides a mild and selective method for the immobilization and cleavage of alcohols, which is crucial in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4-Dihydro-2H-pyran-2-methanol is used as a key intermediate in the synthesis of various drugs and drug candidates. Its ability to protect alcohol functional groups makes it a valuable tool in the development of new medications.
Used in Flavor and Fragrance Industry:
3,4-Dihydro-2H-pyran-2-methanol is also utilized in the flavor and fragrance industry as a building block for the creation of various scent compounds. Its unique chemical structure allows for the development of novel fragrances and flavors.
Used in Material Science:
In the field of material science, 3,4-Dihydro-2H-pyran-2-methanol is employed in the development of new polymers and materials with specific properties. Its versatility in chemical reactions enables the creation of materials with tailored characteristics for various applications.
Overall, 3,4-Dihydro-2H-pyran-2-methanol is a versatile compound with a wide range of applications across different industries, including chemical synthesis, pharmaceuticals, flavor and fragrance, and material science. Its unique chemical properties make it an essential tool in the development of new products and technologies.

InChI:InChI=1/C6H10O2/c7-5-6-3-1-2-4-8-6/h2,4,6-7H,1,3,5H2

Upstream product

• 100-73-2 acrolein dimer 
• 83568-11-0 racem. ethyl 3,4-dihydro-2H-pyran-2-carboxylate 
• 20583-51-1 1SR,5SR-6,8-dioxabicyclo<3.2.1>oct-3-ene 
• 3540-36-1 (3,4-dihydro-2H-pyran-2-yl)methyl 3,4-dihydro-2H-pyran-2-carboxylate 
• 74-88-4 methyl iodide 
• 16698-52-5 3,4-dihydro-2H-pyran-2-carboxylic acid sodium salt 

Downstream Products

• 106-69-4 hexane-1,2,6-triol 
• 22347-71-3 acetic acid 3,4-dihydro-2H-pyran-2-ylmethyl ester 
• 194861-23-9 2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran 
• 7007-32-1 (3,4-Dihydro-2H-pyran-2-yl)methyl 4-Methylbenzenesulfonate 
• 100-73-2 acrolein dimer 
• 319426-10-3 tert-butyl-[4-(3,4-dihydro-2H-pyran-2-ylmethoxy)-phenoxy]-dimethyl-silane 
• 873309-58-1 tert-butyl ((3,4-dihydro-2H-pyran-2-yl)methoxy)diphenylsilane 
• 287176-40-3 2-Benzyl-3,4-dihydro-2H-pyran 
• 287176-45-8 [phenyl-⁽²⁾H₅]-2-Benzyl-3,4-dihydro-2H-pyran 

Relevant articles and documents

Hydroxypurine compound and use thereof

The invention discloses a hydroxypurine compound and a use of the hydroxypurine compound as a PDE2 or TNFa inhibitor and concretely discloses a compound shown in the formula (I) and its tautomer or pharmaceutically acceptable salt.

Towards a library of chromene cannabinoids: A combinatorial approach on solid supports

A novel solid-phase synthesis towards classical cannabinoids is presented. Starting from immobilized salicylaldehydes the desired THC-analogous tricycles are obtained in four atom-economic steps including cleavage. The reagents of the employed reactions (domino oxa-Michael-aldol, Wittig, and Diels-Alder) can be varied easily, providing the basis for a combinatorial approach. Overall yields range from 20-60%. Georg Thieme Verlag Stuttgart New York.

Design, synthesis, and preliminary SAR study of 3- and 6-side-chain-extended tetrahydro-pyran analogues of cis- and trans-(6-benzhydryl-tetrahydropyran-3-yl)-benzylamine

In our effort to further understand interaction of novel pyran derivatives with monoamine transporters, we have designed, synthesized, and biologically characterized side-chain-extended derivatives of our earlier developed cis- and trans-(6-benzhydryl-tetrahydro-pyran-3-yl)-benzylamine derivatives. Both 3- and 6-position extensions were explored. All synthesized derivatives were tested for their affinities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) in the brain by measuring their potency in inhibiting the uptake of [3H]DA, [3H]5-HT, and [3H]NE, respectively. Compounds were also tested for their binding affinity at the DAT by their ability to inhibit binding of [3H]WIN 35, 428. The results indicated that extension at the 3-position resulted in loss of activity compared to the original compound I. On the other hand, extension at the 6-position resulted in improvement of activity in the compound cis-12 by 2-fold over the parent compound I indicating favorable interaction. In addition, two glycoside derivatives were designed, synthesized, and biologically characterized. The glycosidic trans-isomer 24 exhibited highest potency for the NET in the current series of compounds.

Efficient polymer-assisted strategy for the deprotection of protected oligosaccharides

(Chemical Equation Presented) New strategies in sugar synthesis: A prelinker containing a dihydropyranyl moiety and an activated ester can be attached to a sugar, which is then loaded onto an amino-modified support by amidation. Standard protecting-group manipulations are possible. Final cleavage of the linker under mildly acidic conditions provides the fully deprotected oligosaccharides. TFA=trifluoroacetic acid.

Oxygen to carbon rearrangements of anomerically linked alkenols from tetrahydropyran derivatives: An investigation of the reaction mechanism via a double isotopic labelling crossover study

A variety of alkenol tetrahydropyran derivatives were prepared and subjected to a tin tetrachloride promoted anomeric oxygen to carbon rearrangement. Using this methodology many of the corresponding carbon-linked structures were synthesised, including alkenes and bicyclic ethers, in good yields. On the basis of an isotopic labelling study using 2H incorporated into the side chain and ring system it is proposed that these reactions proceed via an intermodular pathway. The Royal Society of Chemistry 2000.

Enantiopure purpurosamine C type glycosyl donors an improved access from rac-Acrolein dimer - Biocatalytic resolution

An improved synthetic access to a suitably 'protected' purpurosamine C type glycosyl donor (11, analogously ent-11) starting from racemic 3,4-dihydro-2H-pyran-2-carbaldehyde (rac-1, acrolein dimer) implies an 'indirect aziridination protocol' and a biocatalytic resolution step (acetate hydrolysis, ee > 98). The latter's stereochemical course is confirmed by a highly α-selective glycosylation with an acceptor of known absolute configuration.

Antibody-catalyzed hydrolysis of enol ethers. 2. Structure of the antibody - Transition state complex and origin of the enantioselectivity

The hydrolysis of alkyl enol ethers to their corresponding carbonyl compounds proceeds by acid-catalyzed, rate-determining protonation on the β-carbon to form an oxocarbonium ion intermediate (Kresge, A. J.; Chang, Y. J. Chem. Soc. B 1967, 53). Antibody 14D9 (anti-1) catalyzes the hydrolysis of enol ethers 4 and 5 with very high enantioselectivity of protonation (Reymond, J.-L.; Janda, K. D.; Lerner, R. A. J. Am. Chem. Soc. 1992, 114, 2257). Catalysis involves participation of an antibody side chain as a general acid, as well as pyramidalization of the enol ether's β-carbon by hydrophobic contacts between its substituents and the antibody (Reymond, J.-L.; Jahangiri, G. K.; Stoudt, C.; Lerner, R. A. J. Am. Chem. Soc. 1993, 115, 3909). The present study addresses the question of the origin of the enantioselectivity of this catalyst. First, enantioselectivity and substrate tolerance, which are most remarkable in antibody 14D9, are shown to be recurrent features for anti-1 or anti-2 antibodies. Four antibodies were studied, and all enantioselectively deliver a proton on the re face of enol ethers to produce (S)-configured carbonyl products, while stereoselectively binding to analogs of the (S,S)-hapten 1. The orientation of the enol ether at the transition state relative to the hapten is then established by comparing the effect of alkyl substitutions at the β-carbon on antibody catalysis with the effect of equivalent substitutions on antibody binding to hapten analogs. For antibody 14D9 (anti-1), the results show that the alkyl substituent of the enol ether's β-carbon binds to the N-methyl site of the hapten at the transition state. Substitution of ethyl for methyl at that position results in a 20-fold drop in transition state binding and a 3-7-fold drop in affinity for inhibitors. The orientation is such that the cyclic substrates do not fit in the site complementary to the piperidine ring of the hapten at the transition state. The antibody-catalyzed hydrolysis of the cyclopentanone enol ether 6, which produces exclusively (S)-7, is 40 times more efficient than for the cyclohexanone enol ether 10. By contrast, no binding selectivity is found for the individual enantiomers of the corresponding ketone products 7 and 18, which are neutral transition state analogs for re- or si-selective protonation of 6 or 10. The enantioselectivity of 14D9 appears only for the transition state, which suggests that it contains a dynamic component, probably the strict geometrical constraint that the enol ether be aligned with the antibody residue acting as a general acid catalyst during proton transfer. The enantioselectivity of antibody 14D9 thus results from an unexpected combination of binding and catalysis. This study establishes the relationship between hapten and transition states in unprecedented details. The observation that the discriminating power of an antibody for enantiomeric transition states can far exceed simple binding discrimination for ground state molecules suggests a promising future for catalytic antibodies as enantioselective catalysts.

On the Mechanism of Organoaluminum-Promoted Claisen Rearrangement of Allylic Vinyl Ethers

The organoaluminum-promoted Claisen rearrangement of allylic vinyl ethers has been mechanistically studied by two sets of experiments and the observed Z and E selectivity is best accounted for by two possible chair-like structures with R substituents axial and equatorial, respectively.

Determination of the gauche effect of 3-acetamido- and 3-acetoxy-piperidine and -tetrahydropyran by 1H-n.m.r. spectroscopy

The A-values of the acetamido and the acetoxy group were determined by low-temperature 1H-n.m.r. spectroscopy.The limiting values for the relevant vicinal coupling constants of the newly prepared trans- (22) and cis-5-acetoxy-2-(1-hydroxy-1-methylethyl)tetrahydropyran (24) were obtained at room temperature.The attractive gauche effect of AcNH-3 and AcO-3 in piperidines, piperidinium trifluoroacetates, and tetrahydropyrans was investigated by 1H-n.m.r. spectroscopy both at low temperature (integrals) and at room temperature (band widths and coupling constants).The results obtained at low temperature are more reliable.The position of the conformational equilibrium of N-(3-piperidyl)acetamide (11), N-(1-methyl-3-piperidyl)acetamide (12), and N-(tetrahydropyran-3-yl)acetamide (17) depends strongly upon the nature of the solvent and, in apolar solvents, upon the concentration.