[ CAS No. 32780-06-6 ] {[proInfo.proName]}

Name: 32780-06-6|(S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one|95%
Brand: Ambeed
SKU: A437432
Price: 10.0 USD
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3d Animation Molecule Structure of 32780-06-6

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Quality Control of [ 32780-06-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 32780-06-6 ]

Product Details of [ 32780-06-6 ]

CAS No. :	32780-06-6	MDL No. :	MFCD00066224
Formula :	C₅H₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NSISJFFVIMQBRN-BYPYZUCNSA-N
M.W :	116.12	Pubchem ID :	2733813
Synonyms :

Calculated chemistry of [ 32780-06-6 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	26.48
TPSA :	46.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.07
Log Po/w (XLOGP3) :	-0.44
Log Po/w (WLOGP) :	-0.32
Log Po/w (MLOGP) :	-0.38
Log Po/w (SILICOS-IT) :	0.69
Consensus Log Po/w :	0.13

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.22
Solubility :	70.5 mg/ml ; 0.607 mol/l
Class :	Very soluble
Log S (Ali) :	-0.07
Solubility :	98.4 mg/ml ; 0.848 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.16
Solubility :	79.8 mg/ml ; 0.687 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.03

Safety of [ 32780-06-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 32780-06-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 32780-06-6 ]
Downstream synthetic route of [ 32780-06-6 ]

[ 32780-06-6 ] Synthesis Path-Upstream 1~1

1
[ 32780-06-6 ]
[ 24211-54-9 ]

Reference： [1] Journal of Organic Chemistry, 1985, vol. 50, # 6, p. 896 - 899
[2] Synthesis, 1986, vol. NO. 3, p. 232 - 233
[3] Synthetic Communications, 2015, vol. 45, # 13, p. 1559 - 1565

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Yield	Reaction Conditions	Operation in experiment
93%	In dichloromethane at 20℃;	52A To a solution of (S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one (1.0 g, 8.6 mmol, Acros) in dichloromethane (10 mL) were added 3,4-dihydro-2H-pyran (0.94 mL, 10.3 mmol, Aldrich) and pyridinium p-toluenesulfonate (0.22 g, 0.86 mmol, Aldrich). After stirring at room temperature overnight, the reaction mixture was washed with water (5 mL) and brine (5 mL). The organic extract was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography using an Analogix Intelliflash280 (SiO2, 0-100% ethyl acetate in hexanes) to obtain 1.6 g (93%) of the title compound. MS (DCI/NH3) m/z 218 (M+NH4)+
93%	In dichloromethane at 20℃;	52A To a solution of (S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one (1.0 g, 8.6 mmol, Acros) in dichloromethane (10 mL) were added 3,4-dihydro-2H-pyran (0.94 mL, 10.3 mmol, Aldrich) and pyridinium p-toluenesulfonate (0.22 g, 0.86 mmol, Aldrich). After stirring at room temperature overnight, the reaction mixture was washed with water (5 mL) and brine (5 mL). The organic extract was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography using an Analogix Intelliflash280 (SiO2, 0-100% ethyl acetate in hexanes) to obtain 1.6 g (93%) of the title compound. MS (DCI/NH3) m/z 218 (M+NH4)+
88%	With pyridinium 4-toluenesulfonate In dichloromethane at 20℃; Inert atmosphere;	2.3 To a mixture of (S)-5-(hydroxymethyl)-dihydrofuran-2(3H)-one (1.78 g,0.0153 mol) and 3,4-dihydro-2H-pyran (2.62 g, 0.0312 mol, Alfa) in 40 mL Of CH2Cl2 was added PPTS (0.391 g, 0.00156 mol, Aldrich) slowly. After stirring at rt overnight, the reaction mixture was quenched with 5 mL of water. The mixture was extracted with EtOAc (50 mLx2). The combined organic phases were dried over Na2SO4 and concentrated in vacuo to give pale yellow oil. The crude product was purified by a silica gel column chromatography (3 : 1 (v/v) petroleum ether / EtOAc) to afford the title compound as colorless oil (2.7 g, 88 %).MS (ESI, pos. ion) m/z: 200.8 (M+l);1H NMR (400MHz, CDCl3): δl.41 - 1.62 (m, 4H), 1.64 - 1.75 (m, 2H), 2.11 - 2.19 (m, IH), 2.22 - 2.31 (m, IH) , 2.39 - 2.49 (m, IH), 2.51 - 2.62 (m, IH), 3.41 - 3.48 (m, IH), 3.58 - 3.62 (dd, J1=3.2 Hz, J2=14.6 Hz, IH), 3.74 - 3.79 (m, IH), 3.85 - 3.92 (dd, J1=3.2 Hz, J2=14.4 Hz, IH), 4.55 - 4.72 ( m, 2H).

85%	With pyridinium 4-toluenesulfonate In dichloromethane at 20℃; for 16h;	A92.1 Step 1 : (5S)-5-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)dihydrofuran-2(3H)-one (A92-1) To a stirred solution of (S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one (4.0 g, 34.45 mmol) in DCM (20 mL) was added 3,4-dihydro-2H-pyran (3.95 mL, 41.34 mmol) followed by pyridinium p-toluenesulfonate (0.86 g, 3.44 mmol) at room temperature and the mixture was stirred for 16 h. The reaction mixture was diluted with DCM (20 mL), quenched with water (40 mL) and extracted with DCM (2 x 50 mL). The combined organic layers were washed with brine (2 x 20 mL), dried over anhydrous Na2S04, and - concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 50% EtOAc/hexane as eluent) to provide compound A92-1 (5.85 mg, 85%) as a colorless gum.
83%	With pyridinium 4-toluenesulfonate In dichloromethane at 20℃; for 1h;
	With hydrogen cation
	In dichloromethane

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: L-glutamic acid With hydrogenchloride; sodium nitrite at 0 - 20℃; Stage #2: With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 4.5h; Further stages.;
	With dimethylsulfide borane complex; sulfuric acid; sodium nitrite 2.) CHCl₃; Multistep reaction;
	Stage #1: L-glutamic acid With hydrogenchloride; sodium nitrite Stage #2: With dimethylsulfide borane complex In tetrahydrofuran

	Multi-step reaction with 2 steps 1: 85 percent / NaNO₂; HCl / H₂O 2: 88 percent / BH₃*SMe₂ / tetrahydrofuran
	Multi-step reaction with 2 steps 1: sodium nitrite; aq. HCl / 0 - 20 °C 2: 10.0 g / BH₃*Me₂S / tetrahydrofuran / 4 h / 20 °C
	Multi-step reaction with 2 steps 1: NaNO₂; HCl / H₂O 2: borane-dimethylsulfide complex
	Multi-step reaction with 2 steps 1: 63.3 percent / cc. HCl; NaNO₂ / H₂O / 16 h / 22 °C 2: 85.1 percent / BH₃*SMe₂ / tetrahydrofuran / 3 h / 20 °C
	Multi-step reaction with 3 steps 1: NaNO₂; 37 percent aq. HCl / 12 h / 20 °C 2: 10.203 g / H₂SO₄ / 48 h / 20 °C 3: 86 percent / NaBH₄ / ethanol / 2 h / 20 - 25 °C
	Multi-step reaction with 2 steps 1: 49 percent / aq. sodium nitrite; conc. hydrochloric acid / 6 h / 0 - 5 °C 2: 53.1 percent / borane-methyl sulfide reagent / tetrahydrofuran / 3 h
	Multi-step reaction with 2 steps 1: 54 percent / NaNO₂, conc. HCl / H₂O / Ambient temperature 2: 80 percent / 10M BH₃*(CH₃)2S / tetrahydrofuran / 4 h / Ambient temperature
	Multi-step reaction with 2 steps 1: 59 percent / NaNO₂, HCl 2: 76 percent / BH₃*S(CH₃)2 / tetrahydrofuran
	Multi-step reaction with 2 steps 1: 56 percent / sodium nitrite, HCl / H₂O / 1.) 15-20 deg C, 5 h, 2.) RT, overnight 2: borane-dimethyl sulfide (BH₃-SMe₂) / tetrahydrofuran / 2 h / Ambient temperature
	Multi-step reaction with 2 steps 1: 10 g / nitrite de sodium, 1N acide sulfurique / H₂O 2: 2N BH₃-Me₂S complex / tetrahydrofuran / 1 h
	Multi-step reaction with 2 steps 1: 74 percent 2: 83 percent / 2N borane dimethylsulfide / tetrahydrofuran / 15 h / 0 °C
	Multi-step reaction with 2 steps 1: NaNO₂, H₃O⁺ 2: BH₃*SMe₂ / tetrahydrofuran / 20 °C
	Multi-step reaction with 3 steps 1: HNO₂ 2: H⁽¹⁺⁾ 3: NaBH₄
	Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / water / 0 - 20 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: hydrogenchloride; sodium nitrite / water 2: toluene-4-sulfonic acid 3: sodium tetrahydroborate / ethanol
	Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / water / 0 - 20 °C / Inert atmosphere 2: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 20 °C
	Multi-step reaction with 2 steps 1: sodium nitrite; hydrogenchloride / water / 0 - 5 °C / Inert atmosphere; Large scale 2: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere; Large scale
	Multi-step reaction with 2 steps 1: sodium nitrite; hydrogenchloride / water 2: dimethylsulfide borane complex
	Multi-step reaction with 2 steps 1: sodium nitrite; hydrogenchloride / water 2: dimethylsulfide borane complex
	Multi-step reaction with 2 steps 1: cis-nitrous acid; hydrogenchloride / water / 8 h / 0 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 20 °C
	Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / water / -5 - 20 °C / Inert atmosphere 2: dimethylsulfide borane complex / tetrahydrofuran / -20 - 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: sodium nitrite; hydrogenchloride / water / 0 - 20 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / water / 23 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 2: dimethylsulfide borane complex / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
	Multi-step reaction with 2 steps 1: sulfuric acid; sodium nitrite / water / 15 h / 20 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 12 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1: sodium nitrite; sulfuric acid 2: toluene-4-sulfonic acid 3: sodium tetrahydroborate / ethanol
	Multi-step reaction with 2 steps 1: sulfuric acid; sodium nitrite / water / 15 h / 0 - 20 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: sodium nitrite; hydrogenchloride / water / 0 - 20 °C 2: dimethyl sulfide borane / tetrahydrofuran / 0 °C
	Multi-step reaction with 2 steps 1: sodium nitrite; hydrogenchloride / water / 16 h / 0 - 20 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite; water / 18 h / 0 - 20 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 18 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: sodium nitrite; hydrogenchloride / water / 24 h / 23 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 0 °C

[ CAS No. 32780-06-6 ] {[proInfo.proName]}

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