Production Method 1

141-46-8

96-26-4

95-43-2

551-84-8

Reaction Conditions

1.1 Catalysts: Fructose-6-phosphate aldolase

Reference

Engineering the Donor Selectivity of D-Fructose-6-Phosphate Aldolase for Biocatalytic Asymmetric Cross-Aldol Additions of Glycolaldehyde

Szekrenyi, Anna; Soler, Anna; Garrabou, Xavier; Guerard-Helaine, Christine; Parella, Teodor; et al, Chemistry - A European Journal, 2014, 20(39), 12572-12583

Production Method 2

141-46-8

95-43-2

Reaction Conditions

1.1 Catalysts: Fructose-6-phosphate aldolase Solvents: Water ;  24 h, pH 7, rt

Reference

Biocatalytic construction of quaternary centers by aldol addition of 3,3-disubstituted 2-oxoacid derivatives to aldehydes

Marin-Valls, Roser; Hernandez, Karel; Bolte, Michael ; Parella, Teodor ; Joglar, Jesus; et al, Journal of the American Chemical Society, 2020, 142(46), 19754-19762

Production Method 3

2418-52-2

95-43-2

Reaction Conditions

1.1 Reagents: Sulfuric acid Catalysts: Platinum ,  Carbon

Reference

Selective Electrocatalytic Oxidation of Sorbitol to Fructose and Sorbose

Kwon, Youngkook; de Jong, Ed; van der Waal, Jan Kees; Koper, Marc T. M., ChemSusChem, 2015, 8(6), 970-973

Production Method 4

141-46-8

95-43-2

Reaction Conditions

1.1 Catalysts: Fructose-6-phosphate aldolase Solvents: Water ;  24 h, pH 7.5, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 3, rt
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 6, rt

Reference

Efficient biocatalytic processes for highly valuable terminally phosphorylated C5 to C9 D-ketoses

Guerard-Helaine, C.; Debacker, M.; Clapes, P.; Szekrenyi, A.; Helaine, V.; et al, Green Chemistry, 2014, 16(3), 1109-1113

Production Method 5

530-27-8

95-43-2

Reaction Conditions

1.1 Reagents: Acetic acid ,  Oxalic acid ,  Lead tetraacetate

Reference

Applications of an asymmetric [2 + 2]-photocycloaddition. Total synthesis of (-)-echinosporin. Construction of an advanced 11-deoxyprostaglandin intermediate

Smith, Amos B. III; Sulikowski, Gary A.; Sulikowski, Michelle M.; Fujimoto, Katsumi, Journal of the American Chemical Society, 1992, 114(7), 2567-76

Production Method 6

111205-93-7

95-43-2

Reaction Conditions

1.1 Reagents: Perchloric acid Solvents: Tetrahydrofuran ,  Water

Reference

Reaction of 2,3-O-isopropylidene-D-glyceraldehyde with ethyl ethylthiomethyl sulfoxide

Lopez Sastre, J. A.; Sanz Tejedor, A.; Rodriguez Amo, J. F.; Molina Molina, J.; Izquierdo Cubero, I., Anales de Quimica, 1986, 82(2), 140-3

Production Method 7

95-43-2

Reaction Conditions

Reference

Method for preparation of aldotetroses by photocatalytic reaction of aldonic acid salts or aldonic acid δ-lactones

, Japan, , ,

Production Method 8

95-43-2

Reaction Conditions

Reference

D-fructose-6-phosphate aldolase in organic synthesis: Cascade chemical-enzymatic preparation of sugar-related polyhydroxylated compounds

Concia, Alda Lisa; Lozano, Carles; Castillo, Jose A.; Parella, Teodor; Joglar, Jesus; et al, Chemistry - A European Journal, 2009, 15(15), 3808-3816

Production Method 9

95-43-2

Reaction Conditions

Reference

Oxidative decarboxylation of aldonolactones by cerium(IV) sulfate in aqueous sulfuric acid. Part II. Mechanism and kinetics; synthesis of D-lyxose, D-erythrose and D-threose

Sala, L. F.; Fernandez Cirelli, A.; De Lederkremer, R. M., Anales de la Asociacion Quimica Argentina, 1978, 66(1), 57-63

Production Method 10

95-43-2

Reaction Conditions

Reference

Use of a Grignard reagent to lengthen a triose carbon chain

Walton, Donald J., Canadian Journal of Chemistry, 1967, 45(23), 2921-5

Production Method 11

141-46-8

95-43-2

Reaction Conditions

1.1 Catalysts: Fructose-6-phosphate aldolase Solvents: Water ;  24 h, rt

Reference

Asymmetric assembly of aldose carbohydrates from formaldehyde and glycolaldehyde by tandem biocatalytic aldol reactions

Szekrenyi, Anna; Garrabou, Xavier; Parella, Teodor; Joglar, Jesus; Bujons, Jordi; et al, Nature Chemistry, 2015, 7(9), 724-729

Production Method 12

141-46-8

95-43-2

Reaction Conditions

1.1 Reagents: Sodium bicarbonate ,  Hydrochloric acid Catalysts: Fructose-6-phosphate aldolase Solvents: Water ;  24 h, pH 7.7, rt
1.2 Reagents: Methanol

Reference

Asymmetric Self- and Cross-Aldol Reactions of Glycolaldehyde Catalyzed by D-Fructose-6-phosphate Aldolase

Garrabou, Xavier; Castillo, Jose A.; Guerard-Helaine, Christine; Parella, Teodor; Joglar, Jesus; et al, Angewandte Chemie, 2009, 48(30), 5521-5525

Production Method 13

141-46-8

95-43-2

Reaction Conditions

1.1 Catalysts: D-threo-Hexos-5-ulose, 2,6-dideoxy-, 1-(dimethyl acetal) Solvents: Water ;  overnight, rt

Reference

Efficient immobilization of fructose-6-phosphate aldolase in layered double hydroxide: improved stereoselective synthesis of sugar analogues

Guerard-Helaine, Christine; Legeret, Bertrand; Fernandes, Carlos; Prevot, Vanessa; Forano, Claude; et al, New Journal of Chemistry, 2011, 35(4), 776-779

Production Method 14

141-46-8

95-43-2

Reaction Conditions

1.1 Reagents: NAD Catalysts: L-Fucose dehydrogenase Solvents: Water ;  pH 8

Reference

Process for the production of 2,4-dihydroxybutyrate or L-threonine by use of a microbial metabolic pathway

, Germany, , ,

Production Method 15

109848-57-9

95-43-2

Reaction Conditions

Reference

Silver(I) carbonate on celite

Fetizon, Marcel, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-6

Production Method 16

95-43-2

Reaction Conditions

Reference

Process for the production of an aldose derivative

, European Patent Organization, , ,

Production Method 17

496-55-9

95-43-2

583-50-6

Reaction Conditions

1.1 Catalysts: Ammonium tungsten oxide Solvents: Water ;  30 s, 190 °C; cooled
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 7

Reference

Efficient Production of Biomass-Derived C4 Chiral Synthons in Aqueous Solution

Lin, Shaoying; Guo, Xiao; Qin, Kai; Feng, Lei; Zhang, Yahong ; et al, ChemCatChem, 2017, 9(22), 4179-4184

Production Method 18

141-46-8

95-43-2

583-50-6

Reaction Conditions

1.1 Catalysts: L-Hydroxyproline Solvents: Water ;  16 h, rt

Reference

Amino acid catalyzed neogenesis of carbohydrates: A plausible ancient transformation

Cordova, Armando; Ibrahem, Ismail; Casas, Jesus; Sunden, Henrik; Engqvist, Magnus; et al, Chemistry - A European Journal, 2005, 11(16), 4772-4784

Production Method 19

583-50-6

95-43-2

25691-81-0

496-55-9

Reaction Conditions

1.1 Catalysts: Ammonium molybdenum oxide Solvents: Water

Reference

Reactions of saccharides catalyzed by molybdate ions. XLVII. Effect of molybdate ions on transformation of lower aldoses

Konigstein, J.; Bilik, V., Chemical Papers, 1992, 46(4), 257-60

Production Method 20

23147-58-2

95-43-2

533-49-3

583-50-6

95-44-3

Reaction Conditions

1.1 Catalysts: 2882064-88-0 (Zn-complexes) ;  2 h, rt

Reference

Mechano-catalysis boosts glycolaldehyde conversion to tetroses over a new Zn-COF catalyst

Yang, Junxia; Fang, Xu; Ren, Guoqing; Yu, Tie, New Journal of Chemistry, 2023, 47(2), 558-562

Production Method 21

141-46-8

95-43-2

533-49-3

583-50-6

95-44-3

Reaction Conditions

1.1 Solvents: Water ;  48 h, rt

Reference

Catalytic Gels for a Prebiotically Relevant Asymmetric Aldol Reaction in Water: From Organocatalyst Design to Hydrogel Discovery and Back Again

Hawkins, Kirsten; Patterson, Anna K.; Clarke, Paul A.; Smith, David K., Journal of the American Chemical Society, 2020, 142(9), 4379-4389

D-Threose (~0.4 M aqueous solution) Raw materials

• Acetaldehyde, hydroxy-(9CI)
• alpha-D-Pyranose-form-Talose,
• Glycoaldehyde Dimer
• Dihydroxyacetone
• (2R,3R)-4-(Formyloxy)-2,3-dihydroxybutanal
• D-Erythrose
• D-Threitol
• D-Erythrulose (~0.3 M in Water, ~90%)
• α-[(Ethylsulfinyl)(ethylthio)methyl]-2,2-dimethyl-1,3-dioxolane-4-methanol

D-Threose (~0.4 M aqueous solution) Preparation Products

• D-Threose (~0.4 M aqueous solution) (95-43-2)
• D-Xylulose (0.5 M in Water) (551-84-8)
• L-Erythrose (~0.1 M solution in water) (533-49-3)
• (3R)-3,4-Dihydroxy-2-oxobutanal (25691-81-0)
• D-Erythrose (583-50-6)
• D-Erythrulose (~0.3 M in Water, ~90%) (496-55-9)
• L-Threose (95-44-3)

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• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Monosaccharides
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Monosaccharides

• 68921-30-2(d-Glucose, enzyme-hydrolyzed)
• 74182-37-9(D-Galactose-1-C-t (9CI))
• 6829-62-5(D-ribo-Hexose, 5-deoxy-)
• 634-74-2((2S,3S,4R,5R)-2,3,4,5-Tetrahydroxyhexanal)
• 533-49-3(L-Erythrose (~0.1 M solution in water))
• 7558-94-3(Butanal, 2,3,4-trihydroxy-)
• 1758-51-6(Butanal,2,3,4-trihydroxy-, (2R,3R)-rel-)
• 6027-89-0(L-Gulose)
• 583-50-6(D-Erythrose)
• 62475-58-5(D-Glucoheptose)