(2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Base Information

• Chemical Name: (2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
• CAS No.: 530-26-7
• Deprecated CAS: 147-74-0,50986-23-7,50986-24-8,149014-30-2,530-26-7,149014-30-2,50986-24-8
• Molecular Formula: C6H12O6
• Molecular Weight: 180.158
• Hs Code.: 2932999099
• UNII: PHA4727WTP
• DSSTox Substance ID: DTXSID5040463
• Nikkaji Number: J82.111J
• Wikidata: Q27117223
• NCI Thesaurus Code: C83903
• Metabolomics Workbench ID: 55657
• Mol file: 530-26-7.mol

Synonyms:D Mannose;D-Mannose;Mannopyranose;Mannopyranoside;Mannose

Chemical Property of (2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Chemical Property:

• Boiling Point: 410.8±45.0 °C(Predicted)
• PKA: pKa: 12.08(25°C)
• PSA: 110.38000
• Density: 1.732±0.06 g/cm3(Predicted)
• LogP: -3.22140
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 180.06338810
• Heavy Atom Count: 12
• Complexity: 138

Purity/Quality:

98%min ^*data from raw suppliers

Mannose United States Pharmacopeia (USP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(C(C(C=O)O)O)O)O)O
• Isomeric SMILES: C([C@H]([C@H]([C@@H]([C@@H](C=O)O)O)O)O)O

Technology Process of (2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

There total 79 articles about (2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal 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: 72.0%

methanol (67-56-1) + sucrose → D-Mannose (530-26-7) + (S)-Methyl lactate (27871-49-4,2155-30-8) + 2-methoxyethyl vinyl ether (1663-35-0) + methyl 2-hydroxybut-3-enoate (5837-73-0) + 1,1-dihydroxyacetone (1186-47-6) + Glyceraldehyde (56-82-6,367-47-5,26793-98-6) + glycoaldehyde diethyl acetal (621-63-6)

Guidance literature:

With potassium carbonate; at 160 ℃; for 16h; Reagent/catalyst; Flow reactor;

Reference yield: 17.0%

phenyl-β-D-glucopyranoside (1464-44-4) → D-Glucose (2280-44-6) + D-Mannose (530-26-7) + levoglucosan (498-07-7)

Guidance literature:

With DCN as sensitizer; In acetonitrile; for 72h; Mechanism; Irradiation;

DOI:10.1016/0008-6215(84)85240-4

Reference yield:

4-nitrophenyl-β-D-mannopyranoside (35599-02-1) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + D-Mannose (530-26-7)

Guidance literature:

With dihydroxy-methyl-borane; water; In various solvent(s); at 25 ℃; Rate constant; pH=11;

DOI:10.1246/cl.1998.1077

upstream raw materials:

D-Glucose

D-<1-3H>mannose

C₂₄H₄₀O₂₂

3-O-(4-O-β-D-mannopyranosyl-α-L-rhamnopyranosyl)-α-D-galactopyranosyl phosphate trethylammonium salt

Downstream raw materials:

N-D-mannopyranosylpiperidine

Methyl mannoside

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

methyl-α,β-D-mannopyranoside

Refernces

• 1、 Athanasopoulos, Vasileios I.,Niranjan, Keshavan,Rastall, Robert A.. "The production, purification and characterisation of two novel α-D-mannosidases from Aspergillus phoenicis". . p. 609 - 617. Retrieved 2005.
• 2、 Mawhinney, Thomas P.,Madson, Michael A.,Feather, Milton S.. "The iomerization of D-glucose in acidic solutions". . p. 147 - 150. Retrieved 1980.
• 3、 Hodosi, Gyoergy,Kovac, Pavol. "Epimerization of carbohydrates via stannylene acetals. A practical synthesis of D-Talose". . p. 557 - 565. Retrieved 1998.
• 4、 Kumagai, Yuya,Yamashita, Keitaro,Tagami, Takayoshi,Uraji, Misugi,Wan, Kun,Okuyama, Masayuki,Yao, Min,Kimura, Atsuo,Hatanaka, Tadashi. "The loop structure of Actinomycete glycoside hydrolase family 5 mannanases governs substrate recognition". . p. 4001 - 4014. Retrieved 2015.
• 5、 Wang, Guei-Jane,Liang, Wen-Li,Ju, Yu-Ming,Yang, Wen-Bin,Chang, Ya-Wen,Lee, Tzong-Huei. "Inhibitory effects of terpenoids from the fermented broth of the ascomycete stilbohypoxylon elaeicola YMJ173 on nitric oxide production in RAW264.7 macrophages". . p. 131 - 138. Retrieved 2012.
• 6、 Smiley-Moreno, Elizabeth,Smith, Douglas,Yu, Jieh-Juen,Cao, Phuong,Arulanandam, Bernard P.,Chambers, James P.. "Biochemical characterization of a recombinant acid phosphatase from Acinetobacter baumannii". . . Retrieved 2021/06/09.
• 7、 -. "A synthesis method of D - mannose (by machine translation)". Paragraph 0027; 0043-0045. . Retrieved 2019/06/07.