(2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanal

Base Information

• Chemical Name: (2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanal
• CAS No.: 2438-80-4
• Deprecated CAS: 87-96-7
• Molecular Formula: C6H12O5
• Molecular Weight: 164.158
• Hs Code.: 29400090
• European Community (EC) Number: 219-452-7
• UNII: 28RYY2IV3F
• DSSTox Substance ID: DTXSID50883845
• Nikkaji Number: J92.797J
• Wikidata: Q105212067
• Metabolomics Workbench ID: 56906
• Mol file: 2438-80-4.mol

Synonyms:alpha Fucose;alpha-Fucose;Deoxygalactose;Fucose

Chemical Property of (2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanal

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 5E-08mmHg at 25°C
• Melting Point: 150-153 °C(lit.)
• Refractive Index: -75.5 ° (C=10, H2O)
• Boiling Point: 399.1 °C at 760 mmHg
• PKA: 12.50±0.20(Predicted)
• Flash Point: 209.3 °C
• PSA: 97.99000
• Density: 1.41 g/cm³
• LogP: -2.35120
• Storage Temp.: -20°C Freezer
• Sensitive.: Hygroscopic
• Solubility.: H2O: 0.1 g/mL, clear, colorless
• Water Solubility.: Soluble in water.
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 164.06847348
• Heavy Atom Count: 11
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

L-Fucose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(C(C(C=O)O)O)O)O
• Isomeric SMILES: C[C@@H]([C@H]([C@H]([C@@H](C=O)O)O)O)O
• Description: L-(?)-Fucose is a deoxyhexose monosaccharide found on N- and O-linked glycans and glycolipids of a wide variety of organisms. It can exist as a terminal modification of glycan structures or serve as a point of attachment for adding other sugars. In humans, L-(?)-fucose plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.
• Uses: L-Fucose was isolated from seaweed. It finds application in cosmetics, pharmaceuticals and dietary supplements. It is used in the determination of antigen in A and B blood group. It is also used in the selection-mediated leukocyte-endothelial adhesion and host-microbe interactions. L-Fucose is also used in anti aging creams as well as to promote the accelerated healing of wounds and to reduce allergy.

Technology Process of (2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanal

There total 137 articles about (2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

N-(tert-butoxycarbonyl)-L-proline 2-(diphenylphosphanyl)-4-fluorophenyl ester (1202249-78-2) + β-L-fucopyranosyl azide (66347-26-0) → L-Fucose (2438-80-4,478518-52-4) + N-(N-tert-butoxycarbonyl-L-prolyl)-β-L-fucopyranosylamine (1202249-91-9)

Guidance literature:

N-(tert-butoxycarbonyl)-L-proline 2-(diphenylphosphanyl)-4-fluorophenyl ester; β-L-fucopyranosyl azide; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-dimethyl acetamide; at 20 - 40 ℃; Inert atmosphere;

With water; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-dimethyl acetamide; at 40 ℃; for 2h;

DOI:10.1002/ejoc.200900692

Reference yield: 75.0%

N-(benzyloxycarbonyl)glycine 2-(diphenylphosphanyl)-4-fluorophenyl ester (1202249-77-1) + β-L-fucopyranosyl azide (66347-26-0) → L-Fucose (2438-80-4,478518-52-4) + N-(N-benzyloxycarbonylglycyl)-β-L-fucopyranosylamine (1202249-90-8) + C16H22N2O7

Guidance literature:

N-(benzyloxycarbonyl)glycine 2-(diphenylphosphanyl)-4-fluorophenyl ester; β-L-fucopyranosyl azide; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-dimethyl acetamide; at 20 - 40 ℃; Inert atmosphere;

With water; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-dimethyl acetamide; at 40 ℃; for 2h;

DOI:10.1002/ejoc.200900692

Reference yield: 74.0%

(2S,3R)-2,2-dimethyl-5-((4'R,5'S)-2',2',5'-trimethyl-1',3'-dioxolan-4'-yl)-1,3-dioxolane-4-carbaldehyde (212065-83-3) → L-Fucose (2438-80-4,478518-52-4)

Guidance literature:

With Dowex (50W X₈, H⁺ form); In water; at 20 ℃; for 24h;

DOI:10.1021/ol502733x

upstream raw materials:

acetic acid

2′-fucosyllactose

(3S,4S,5R)-dihydro-3,4-dihydroxy-5-((1'S)-1'-hydroxyethyl)furan-2(3H)-one

α-L-Fuc-(1-3)-β-D-GalNAc-(1-3)-β-D-Gal-(1-4)-β-D-Gal-(1-3)-D-GalNAc-ol

Downstream raw materials:

L-fuculose

D,L-rhamnose

L-idomethylonic acid

arabino-6-deoxy-[2]hexosulose-bis-phenylhydrazone

Refernces

• 1、 Sinha, Sharmistha,Astani, Akram,Ghosh, Tuhin,Schnitzler, Paul,Ray, Bimalendu. "Polysaccharides from Sargassum tenerrimum: Structural features, chemical modification and anti-viral activity". . p. 235 - 242. Retrieved 2010.
• 2、 Pattanayak, Manabendra,Samanta, Surajit,Maity, Prasenjit,Sen, Ipsita K.,Nandi, Ashis K.,Manna, Dilip K.,Mitra, Payel,Acharya, Krishnendu,Islam, Syed S.. "Heteroglycan of an edible mushroom Termitomyces clypeatus: Structure elucidation and antioxidant properties". . p. 30 - 36. Retrieved 2015.
• 3、 Feng, Tong-Tong,Fu, Hui-Zheng,Yang, Yi-Sheng,Zhou, Zhi-Qiang,Dai, Mian,Bi, Hong-Yu,Wang, Dong. "Two new noroleanane-type triterpenoid saponins from the stems of Stauntonia chinensis". . p. 1269 - 1276. Retrieved 2019.
• 4、 Liu, Dan,Wang, Dandan,Yang, Wei,Meng, Dali. "Potential anti-gout constituents as xanthine oxidase inhibitor from the fruits of Stauntonia brachyanthera". . p. 3562 - 3566. Retrieved 2017.
• 5、 Manikandan, Ramar,Parimalanandhini, Duraisamy,Mahalakshmi, Krishnan,Beulaja, Manikandan,Arumugam, Munuswamy,Janarthanan, Sundaram,Palanisamy, Subramanian,You, SangGuan,Prabhu, Narayanasamy Marimuthu. "Studies on isolation, characterization of fucoidan from brown algae Turbinaria decurrens and evaluation of it's in vivo and in vitro anti-inflammatory activities". . p. 1263 - 1276. Retrieved 2020.
• 6、 Liu, Zilei,Yoshihara, Akihide,Wormald, Mark R.,Jenkinson, Sarah F.,Gibson, Vicky,Izumori, Ken,Fleet, George W.J.. "L-fucose from vitamin C with only acetonide protection". . p. 5663 - 5665. Retrieved 2014.
• 7、 Peng, Tianyuan,Wooke, Zachary,Pohl, Nicola L.B.. "Scope and limitations of carbohydrate hydrolysis for de novo glycan sequencing using a hydrogen peroxide/metallopeptide-based glycosidase mimetic". . p. 85 - 88. Retrieved 2018.
• 8、 Jia, Rui-Bo,Li, Zhao-Rong,Lin, Lianzhu,Luo, Donghui,Ou, Zhi-Rong,Zhao, Mouming,Zheng, Qianwen. "Comparative study on the structural characterization and α-glucosidase inhibitory activity of polysaccharide fractions extracted from Sargassum fusiforme at different pH conditions". . p. 602 - 610. Retrieved 2021/11/30.
• 9、 Cheng, Jiang,Deng, Yejun,Huang, Lixin,Liu, Lujie,Wang, Xiang,Xie, Pujun,Zhang, Caihong. "Novel polysaccharide from Chaenomeles speciosa seeds: Structural characterization, α-amylase and α-glucosidase inhibitory activity evaluation". . p. 755 - 766. Retrieved 2020/03/18.