1883-12-1

Basic information

• Product Name: 3-ketosucrose
• Synonyms: 3-ketosucrose
• CAS NO: 1883-12-1
• Molecular Formula: C₁₂H₂₀O₁₁
• Molecular Weight: 340.2806
• Mol File: 1883-12-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 732.9°C at 760 mmHg
• Flash Point: 276.4°C
• Appearance: /
• Density: 1.77g/cm³
• Vapor Pressure: 8.52E-25mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: 3-ketosucrose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ketosucrose(1883-12-1)
• EPA Substance Registry System: 3-ketosucrose(1883-12-1)

Safety Data

• Hazardous Substances Data: 1883-12-1(Hazardous Substances Data)

Usage

Definition

ChEBI: A glycosyl glycoside which is an intermediate in the breakdown of sucrose. The structure is that of sucrose in which the glucosyl 3-hydroxy group has been reduced to a keto group.

InChI:InChI=1/C12H20O11/c13-1-4-6(15)8(17)9(18)11(22-4)21-2-5-7(16)10(19)12(20,3-14)23-5/h4-7,9-11,13-16,18-20H,1-3H2/t4-,5-,6-,7-,9-,10+,11+,12-/m1/s1

Synthetic route

Sucrose (57-50-1) → 3-ketosucrose (1883-12-1)

Conditions	Yield
With [(2,9-dimethyl-1,10-phenanthroline)-Pd(μ-OAc)]2(OTf)2; p-benzoquinone In dimethylsulfoxide-d6 for 1h; regioselective reaction;	50%
With pyranosedehydrogenase from Agaricus meleagris; p-benzoquinone In water at 25℃; for 24h; Enzymatic reaction;

3-ketoglucose + Sucrose (57-50-1) → 3-ketosucrose (1883-12-1)

Conditions	Yield
With recombinant fructosyltransferase protein extract In phosphate buffer pH=6.0;	5.6%

Sucrose (57-50-1) → 3-ketosucrose (1883-12-1) + β-D-fructofuranosyl α-D-arabino-hexopyranosidulose (78261-84-4)

Conditions	Yield
With Agrobacterium tumefaciens	A 0.9 g B 0.6 g

chloro-trimethyl-silane (75-77-4) + 3-ketosucrose (1883-12-1) → (2,4,6-tri-O-trimethylsilyl)-α-D-ribo-hexopyranosyl-3-ulose-<1-<*>2>-(1',3',4',6'-tetra-O-trimethylsilyl)-β-D-fructofuranoside (158715-85-6)

Conditions	Yield
With pyridine for 4h; Ambient temperature;	76%

3-ketosucrose (1883-12-1) + acetic anhydride (108-24-7) → 1,3,4,6-tetra-O-acetyl-β-D-fructofuranosyl 2,4,6-tri-O-acetyl-α-D-ribo-hexopyranosid-3-ulose

Conditions	Yield
With dmap In N,N-dimethyl-formamide for 0.5h; Ambient temperature;	65%

3-ketosucrose (1883-12-1) → (+)-(2R,3R)-3,5-dihydroxy-2-hydroxymethyl-2,3-dihydro-4H-pyran-4-one (158715-81-2)

Conditions	Yield
With sodium hydroxide for 0.05h; Ambient temperature;	50%

3-ketosucrose (1883-12-1) + acetic anhydride (108-24-7) → allo-sucrose octaacetate (75800-69-0) + 2,3,6-tri-O-acetyl-α-D-allopyranosyl 1,3,4,6-tetra-O-acetyl-β-D-fructofuranoside + 2,4,6-tri-O-acetyl-α-D-allopyranosyl 1,3,4,6-tetra-O-acetyl-β-D-fructofuranoside + sucrose octaacetate (126-14-7)

Conditions	Yield
With pyridine; sodium tetrahydroborate 1.) water, 2.) RT, 15 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;	A n/a B n/a C 37% D n/a

3-ketosucrose (1883-12-1) → 3-ketoglucose

Conditions	Yield
(enzymatic hydrolysis);

3-ketosucrose (1883-12-1) → <3-(2)H>-allosucrose (75754-48-2) + <3-(2)H>-sucrose (75800-71-4)

Conditions	Yield
With sodium borodeuteride In water at 0 - 5℃; for 3h;

3-ketosucrose (1883-12-1) + acetic anhydride (108-24-7) → allo-sucrose octaacetate (75800-69-0)

Conditions	Yield
With sodium tetrahydroborate; sodium acetate 1.) water, 0-5 degC, 24 h; 2.) 100 degC, 2 h; Yield given. Multistep reaction;

3-ketosucrose (1883-12-1) + N-methoxylamine hydrochloride (593-56-6) → β-D-fructofuranosyl 3-methoxyimino-α-D-ribo-hexopyranoside

Conditions	Yield
In water at 60℃; for 2h;

3-ketosucrose (1883-12-1) → 3-(hydroxyimino)-α-D-ribo-hexopyranosyl-β-D-fructofuranoside (158715-82-3)

Conditions	Yield
With hydroxylamine hydrochloride In water at 60℃; for 2h;

3-ketosucrose (1883-12-1) → (2R,3R,5S,6R)-2-((2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-tetrahydro-furan-2-yloxy)-4-hydrazono-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

Conditions	Yield
With hydrazine hydrate In water at 20℃; for 19h; pH=6.0 - 6.5;

3-ketosucrose (1883-12-1) → 3-(L-aspartic acid-4-amido)-3-deoxy-α-D-allopyranose

Conditions	Yield
Multi-step reaction with 6 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: N,N'-dicyclohexylcarbodiimide / pyridine; H2O / 17 h / 20 °C 4: 44 percent / hydrogen / Pd/C / aq. methanol / 4 h / 20 °C 5: 77 percent / aq. trifluoroacetic acid / 0.25 h / 4 °C 6: aq. HCl / 0.17 h / 60 °C View Scheme

3-ketosucrose (1883-12-1) → 3-deoxy-3-glycylamido-α-D-allopyranosyl β-D-fructofuranoside (879291-46-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: 64 percent / ethyl-2-ethoxy-1,2-dihydro-1-quinolinecarboxylate / ethanol; propan-2-ol; H2O / 20 h / 20 °C 4: 95 percent / diethylamine / 1 h / 20 °C View Scheme

3-ketosucrose (1883-12-1) → 3-(L-aspartic acid-4-amido)-3-deoxy-α-D-allopyranosyl β-D-fructofuranoside (879465-22-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: N,N'-dicyclohexylcarbodiimide / pyridine; H2O / 17 h / 20 °C 4: 44 percent / hydrogen / Pd/C / aq. methanol / 4 h / 20 °C 5: 77 percent / aq. trifluoroacetic acid / 0.25 h / 4 °C View Scheme

3-ketosucrose (1883-12-1) → 3-(N-tert-butoxycarbonyl-L-alanylamido)-3-deoxy-α-D-allopyranosyl β-D-fructofuranoside

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: 40 percent / N,N'-dicyclohexylcarbodiimide / pyridine; H2O / 20 °C View Scheme

3-ketosucrose (1883-12-1) → 3-deoxy-3-N'-methacryloyloxyethylureido-α-D-allopyranosyl β-D-fructofuranoside (879291-40-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: 99 percent / H2O / 0 - 7 °C View Scheme

3-ketosucrose (1883-12-1) → 3-(N-tert-butoxycarbonyl-L-leucylamido)-3-deoxy-α-D-allopyranosyl β-D-fructofuranoside

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: 30 percent / N,N'-dicyclohexylcarbodiimide / pyridine; H2O / 20 °C View Scheme

3-ketosucrose (1883-12-1) → 3-(N-tert-butoxycarbonyl-L-aspartic acid-4-amido)-3-deoxy-α-D-allopyranosyl β-D-fructofuranoside (879465-14-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: N,N'-dicyclohexylcarbodiimide / pyridine; H2O / 17 h / 20 °C 4: 44 percent / hydrogen / Pd/C / aq. methanol / 4 h / 20 °C View Scheme

3-ketosucrose (1883-12-1) → 3-(N-tert-butoxycarbonyl-L-phenylalanylamido)-3-deoxy-α-D-allopyranosyl β-D-fructofuranoside

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: 33 percent / N,N'-dicyclohexylcarbodiimide / pyridine; H2O / 20 °C View Scheme

3-ketosucrose (1883-12-1) → 3-(N-tert-butoxycarbonyl-L-aspartic acid-4-amido-1-benzyl ester)-3-deoxy-α-D-allopyranosyl β-D-fructofuranoside (879291-43-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: N,N'-dicyclohexylcarbodiimide / pyridine; H2O / 17 h / 20 °C View Scheme

3-ketosucrose (1883-12-1) → 3-deoxy-3-(N-Fmoc-glycylamido)-α-D-allopyranosyl β-D-fructofuranoside

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: 64 percent / ethyl-2-ethoxy-1,2-dihydro-1-quinolinecarboxylate / ethanol; propan-2-ol; H2O / 20 h / 20 °C View Scheme

3-ketosucrose (1883-12-1) → 3-(Nα-tert-butoxycarbonyl-Nε-L-lysylamido)-3-deoxy-α-D-allopyranosyl β-D-fructofuranoside

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: N,N'-dicyclohexylcarbodiimide / pyridine; H2O / 20 °C View Scheme

3-ketosucrose (1883-12-1) → 3-deoxy-3-(N-Fmoc-L-tryptophanamido)-α-D-allopyranosyl β-D-fructofuranoside

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: 60 percent / ethyl-2-ethoxy-1,2-dihydro-1-quinolinecarboxylate / various solvents / 72 h View Scheme

3-ketosucrose (1883-12-1) → 3-deoxy-3-(N-Fmoc-L-phenylalanyl-glycylamido)-α-D-allopyranosyl β-D-fructofuranoside

Conditions

Yield

Multi-step reaction with 5 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: 64 percent / ethyl-2-ethoxy-1,2-dihydro-1-quinolinecarboxylate / ethanol; propan-2-ol; H2O / 20 h / 20 °C 4: 95 percent / diethylamine / 1 h / 20 °C 5: 50 percent / ethyl-2-ethoxy-1,2-dihydro-1-quinolinecarboxylate / ethanol / 45 h / 20 °C View Scheme

3-ketosucrose (1883-12-1) → 3-amino-3-deoxy-α-D-allopyranosyl β-D-fructofuranoside (121784-13-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr View Scheme

3-ketosucrose (1883-12-1) → 3-deoxy-3-(N-methacrylamido)-α-D-allopyranosyl-β-D-fructofuranoside (158715-83-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrazine hydrate / H2O / 19 h / 20 °C / pH 6.0 - 6.5 2: 95.2 g / hydrogen / Raney alloy / 24 h / 50 °C / 60004.8 Torr 3: 69 percent / methanol / -10 - 4 °C View Scheme

3-ketosucrose (1883-12-1) → (+)-(2R,3R)-3,5-Bis(benzoyloxy)-2-(benzoyloxymethyl)-2,3-dihydro-4H-pyran-4-one (72076-13-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / 1.2 N aq. NaOH / 0.05 h / Ambient temperature 2: 81 percent / pyridine / 3 h / Ambient temperature View Scheme

3-ketosucrose (1883-12-1) → (2R,3R)‐3,5‐diacetoxy‐2‐(acetoxymethyl)‐2,3‐dihydro‐4H‐pyran‐4‐one (41107-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / 1.2 N aq. NaOH / 0.05 h / Ambient temperature 2: 78 percent / pyridine / 0.5 h / Ambient temperature View Scheme

Upstream product

• 57-50-1 Sucrose 

Downstream Products

• 75800-69-0 allo-sucrose octaacetate 
• 126-14-7 sucrose octaacetate 
• 158715-81-2 (+)-(2R,3R)-3,5-dihydroxy-2-hydroxymethyl-2,3-dihydro-4H-pyran-4-one 
• 72076-13-2 (+)-(2R,3R)-3,5-Bis(benzoyloxy)-2-(benzoyloxymethyl)-2,3-dihydro-4H-pyran-4-one 
• 879291-43-7 3-(N-tert-butoxycarbonyl-L-aspartic acid-4-amido-1-benzyl ester)-3-deoxy-α-D-allopyranosyl β-D-fructofuranoside 

Relevant articles and documents

Regioselective oxidation of unprotected 1,4 linked glucans

Palladium-catalyzed alcohol oxidation allows the chemo- and regioselective modification of unprotected 1,4 linked glucans. This is demonstrated in the two-step bisfunctionalization of 1,4 linked glucans up to the 7-mer. Introduction of an anomeric azide is followed by a highly regioselective mono-oxidation of the terminal C3-OH functionality. The resulting orthogonal bis-functionalized oligosaccharides are a viable alternative to PEG-spacers as demonstrated in the conjugation of a cysteine mutant of 4-oxalocrotonate tautomerase with biotin.

Synthesis of sucrose analogues and the mechanism of action of Bacillus subtilis fructosyltransferase (levansucrase)

In the present study, we have coupled detailed acceptor and donor substrate studies of the fructosyltransferase (FTF, levansucrase) (EC 2.4.1.162) from Bacillus subtilis NCIMB 11871, with a structural model of the substrate enzyme complex in order to investigate in detail the roles of the active site amino acids in the catalytic action of the enzyme and the scope and limitation of substrates. Therefore we have isolated the ftf gene, expressed in Escherichia coli, yielding a levansucrase. Consequently, detailed acceptor property effects in the fructosylation by systematic variation of glycoside acceptors with respect to the positions (2, 3, 4 and 6) of the hydroxyl groups from equatorial to axial have been studied for preparative scale production of new oligosaccharides. Such investigations provided mechanistic insights of the FTF reaction. The configuration and the presence of the C-2 and C-3 hydroxyl groups of the glucopyranoside derivatives either as substrates or acceptors have been identified to be rate limiting for the trans-fructosylation process. The rates are rationalized on the basis of the coordination of d-glycopyranoside residues in 4C1 conformation with a network of amino acids by Arg360, Tyr411, Glu342, Trp85, Asp247 and Arg246 stabilization of both acceptors and substrates. In addition we also describe the first FTF reaction, which catalyzes the β-(1→2)-fructosyl transfer to 2-OH of l-sugars (l-glucose, l-rhamnose, l-galactose, l-fucose, l-xylose) presumably in a 1C4 conformation. In those conformations, the l-glycopyranosides are stabilized by the same hydrogen network. Structures of the acceptor products were determined by NMR and mass spectrometry analysis.