32746-79-5

Basic information

• Product Name: δ-D-Mannonolactone
• Synonyms: D-Mannonic acid 1,5-lactone;delta-D-Mannonolactone
• CAS NO: 32746-79-5
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.14
• Mol File: 32746-79-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 23-25 °C
• Boiling Point: 104 °C(Press: 0.02 Torr)
• Appearance: /
• Density: 1.720±0.06 g/cm3(Predicted)
• PKA: 12.13±0.70(Predicted)
• CAS DataBase Reference: δ-D-Mannonolactone(CAS DataBase Reference)
• NIST Chemistry Reference: δ-D-Mannonolactone(32746-79-5)
• EPA Substance Registry System: δ-D-Mannonolactone(32746-79-5)

Safety Data

• Hazardous Substances Data: 32746-79-5(Hazardous Substances Data)

Usage

Uses

D-Mannono-1,5-lactone is an intermediate used in the synthesis of Dapagliflozin C2 Epimer (D185405), which is an intermediate used in the synthesis of Dapagliflozin (D185370), a sodium-glucose transporter 2 inhibitor.

Synthetic route

mannonic acid (642-99-9) → D-mannono-1,4-lactone (26301-79-1) + δ-D-mannonolactone (32746-79-5)

Conditions	Yield
With water at 25℃;
With 1,4-dioxane Eindampfen unter vermindertem Druck;

D-Mannose (530-26-7) → δ-D-mannonolactone (32746-79-5)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid; mercury(II) diacetate In water; acetic acid at 26.9℃; Kinetics; Thermodynamic data; Mechanism; further temperatures, also with Ru(III) as a catalyst; ΔG(excit.), ΔS(excit.), ΔH(excit.), Ea;
With silver nitrate at 80 - 130℃; Thermodynamic data; Rate constant; Equilibrium constant; pH 1, other oxidants, DΕ excit, DΣ excit, DΦ, DΗ;
With potassium dichromate; perchloric acid In water at 60℃; for 1h; Kinetics; Activation energy; Further Variations:; Reagents; Catalysts; Temperatures; Solvents;
With bromine; barium carbonate In water

sodium-mannonate → δ-D-mannonolactone (32746-79-5)

Conditions	Yield
With acetic acid

aqueous d-mannonic acid-solution → δ-D-mannonolactone (32746-79-5) + γ lactone

Conditions	Yield
at 50 - 90℃; under 15 Torr; beim Eindampfen;

D-Mannose (530-26-7) → D-mannono-1,4-lactone (26301-79-1) + δ-D-mannonolactone (32746-79-5)

Conditions	Yield
[(C4Ph4CO)(CO)2Ru]2 In cyclohexanone; N,N-dimethyl-formamide at 21℃; for 87h; Title compound not separated from byproducts;

D-Mannose (3458-28-4) → δ-D-mannonolactone (32746-79-5)

Conditions	Yield
With quinoprotein D-glucose dehydrogenase Enzymatic reaction;

C20H18N2O + δ-D-mannonolactone (32746-79-5) → N-D-mannonyl-N'-1-pyrenemethyl-β-alaninamide

Conditions	Yield
In methanol for 6h; Heating;	67.2%

C20H18N2O + δ-D-mannonolactone (32746-79-5) → N-D-mannonyl-N'-1-pyrenemethyl-L-alaninamide

Conditions	Yield
In methanol for 6h; Heating;	65%

C19H16N2O + δ-D-mannonolactone (32746-79-5) → N-D-mannonyl-N'-1-pyrenemethylglycinamide

Conditions	Yield
In methanol for 6h; Heating;	58%

C20H18N2O + δ-D-mannonolactone (32746-79-5) → N-D-mannonyl-N'-1-pyrenemethyl-D-alaninamide

Conditions	Yield
In methanol for 6h; Heating;	56%

acetic anhydride (108-24-7) + δ-D-mannonolactone (32746-79-5) → 2,3,4,6-tetra-O-acetyl-D-mannono-1,5-lactone (61259-48-1, 73322-42-6)

Conditions	Yield
With hydrogenchloride

δ-D-mannonolactone (32746-79-5) → fructonic acid (669-90-9)

Conditions	Yield
With iron(III) sulfate; water; calcium carbonate und Chrom(VI)-oxid;

δ-D-mannonolactone (32746-79-5) → D-mannono-1,4-lactone (26301-79-1)

Conditions	Yield
With water at 100℃;

1-(Trimethylsilyl)imidazole (18156-74-6) + δ-D-mannonolactone (32746-79-5) → trimethylsilyl ether of mannono-1,5-lactone (32469-28-6)

Conditions	Yield
With pyridine hydrochloride In various solvent(s)

methanol (67-56-1) + 2,2-dimethoxy-propane (77-76-9) + δ-D-mannonolactone (32746-79-5) → methyl 3,4:5,6-di-O-isopropylidene-D-gluconate (114743-85-0)

Conditions	Yield
With methanesulfonic acid In acetone for 48h; Ambient temperature; Yield given;

δ-D-mannonolactone (32746-79-5) + methyl iodide (74-88-4) + silver oxide → O2,O3,O5,O6-tetramethyl-D-mannonic acid-lactone (20869-29-8)

Conditions	Yield
erst in Methanol, dann in Aceton;

δ-D-mannonolactone (32746-79-5) → (4R,5S)-4-Amino-5-((R)-1,2-dihydroxy-ethyl)-dihydro-furan-2-one; hydrobromide

Conditions	Yield
Multi-step reaction with 6 steps 1: MsOH / acetone / 48 h / Ambient temperature 2: pyridine / 1.) 0 deg C, 1 h, 2.) r.t., 1 h 3: 46 percent / aq. ammonia / 120 h 4: 100 percent / N2H4 / H2O / 2 h / Heating 5: TFA, H2O / 1 h / Ambient temperature 6: Br2 / H2O View Scheme

δ-D-mannonolactone (32746-79-5) → (3R,4S,5R)-3-Amino-4,5,6-trihydroxy-hexanoic acid hydrazide

Conditions	Yield
Multi-step reaction with 5 steps 1: MsOH / acetone / 48 h / Ambient temperature 2: pyridine / 1.) 0 deg C, 1 h, 2.) r.t., 1 h 3: 46 percent / aq. ammonia / 120 h 4: 100 percent / N2H4 / H2O / 2 h / Heating 5: TFA, H2O / 1 h / Ambient temperature View Scheme

δ-D-mannonolactone (32746-79-5) → (2R,3R)-3-[(S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-aziridine-2-carboxylic acid amide (204059-79-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: MsOH / acetone / 48 h / Ambient temperature 2: pyridine / 1.) 0 deg C, 1 h, 2.) r.t., 1 h 3: 46 percent / aq. ammonia / 120 h View Scheme

δ-D-mannonolactone (32746-79-5) → (3R,4S)-3-Amino-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-butyric acid hydrazide (204059-86-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: MsOH / acetone / 48 h / Ambient temperature 2: pyridine / 1.) 0 deg C, 1 h, 2.) r.t., 1 h 3: 46 percent / aq. ammonia / 120 h 4: 100 percent / N2H4 / H2O / 2 h / Heating View Scheme

δ-D-mannonolactone (32746-79-5) → (R)-Methanesulfonyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetic acid methyl ester (117462-56-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: MsOH / acetone / 48 h / Ambient temperature 2: pyridine / 1.) 0 deg C, 1 h, 2.) r.t., 1 h View Scheme

δ-D-mannonolactone (32746-79-5) → (2R,3R)-3-[(S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-1-(toluene-4-sulfonyl)-aziridine-2-carboxylic acid amide

Conditions	Yield
Multi-step reaction with 4 steps 1: MsOH / acetone / 48 h / Ambient temperature 2: pyridine / 1.) 0 deg C, 1 h, 2.) r.t., 1 h 3: 46 percent / aq. ammonia / 120 h 4: 37 percent / pyridine / 2 h / 0 °C View Scheme

δ-D-mannonolactone (32746-79-5) → 2,6-Dibromo-2,6-dideoxy-D-glucono-1,4-lactone (78138-23-5)

Conditions	Yield
With hydrogen bromide; acetic acid In water at 20℃; for 4h;	4.6 g

Upstream product

• 642-99-9 mannonic acid 
• 530-26-7 D-Mannose 
• 3458-28-4 D-Mannose 
• 740753-96-2 L-allonic acid 

Downstream Products

• 669-90-9 fructonic acid 
• 26301-79-1 D-mannono-1,4-lactone 
• 78184-43-7 L-mannonic γ-lactone 
• 114743-85-0 methyl 3,4:5,6-di-O-isopropylidene-D-gluconate 

Relevant articles and documents

Enantioselective and protecting group-free synthesis of 1-deoxythionojirimycin, 1-deoxythiomannojirimycin, and 1- deoxythiotalonojirimycin

1-Deoxythioglyconojirimycins were synthesized by using a protecting group-free strategy, starting from readily available carbohydrates, in good overall yield. Use of benzyltriethylammonium tetrathiomolybdate, [BnEt 3N]2MoS4, as a sulfur transfer reagent and borohydride exchange resin (BER) reduction of a lactone enabled the efficient synthesis of the title compounds.

Redox behaviour of chromium(VI) towards D-mannose in the presence and absence of micelles and inorganic salts

The kinetics and mechanism of the oxidation of D-mannose by chromium(VI) in the absence and presence of sodium dodecyl sulfate(SDS) and polyoxylethylene t-octylphenol(TX-100) micelles have been investigated. Under pseudo-first-order conditions the reaction rate is of fractional- and first-order, respectively, in D-mannose and oxidant. The reaction is catalyzed by the micelles which is due to favourable electrostatic/thermodynamic/hydrophobic/hydrogen bonding between the reactants and anionic/nonionic micelles. From the observed kinetic data micelle-chromium(VI) binding constants(KS) and micelle-D-mannose binding constants(KM) were calculated to be 86, 84 mol-1 dm3 and 58, 75 mol-1 dm3 for SDS and TX-100, respectively. The reaction is retarded by addition of inorganic salts (NaBr, LiBr, NH4Br) which is attributed to competition between salt cations and H+ from the reaction sites in the SDS micelles.

Kinetics of Ru(III) Catalysed Oxidation of Aldoses by N-Bromosuccinimide in Aqueous Acetic Acid

The title reaction, studied in the presence of mercuric acetate, sulphuric acid and 10percent (v/v) acetic acid, is first order in both in the presence and absence of catalyst.However, the order in in the absence of catalyst, Ru(III) is unity which changes to fractional order in the presence of it.Increase in retards the reaction rate.The order of reactivities of different aldoses is: D-arabinose > D-xylose > D-galactose > D-mannose > D-glucose.Individual rate constants (k), formation constants (K) of the complex of aldoses and the catalyst and corresponding thermodynamic parameters have been evaluated and a suitable mechanism involving the α-anomer of aldose as the reactive substrate species has been suggested.