(2S,3S,4S,5S)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid

Base Information

• Chemical Name: (2S,3S,4S,5S)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid
• CAS No.: 6814-36-4
• Deprecated CAS: 577-46-8
• Molecular Formula: C₆H₁₀O₇
• Molecular Weight: 194.141
• UNII: 980IT47Y34
• DSSTox Substance ID: DTXSID10218316,DTXSID80873875
• Nikkaji Number: J265.100I
• Wikidata: Q27272055
• ChEMBL ID: CHEMBL4580937
• Mol file: 6814-36-4.mol

Synonyms:beta-D-mannuronic acid;M2000 mannuronic acid;mannuronic acid;mannuronic acid, (beta-D)-isomer;mannuronic acid, (D)-isomer;mannuronic acid, (L)-isomer

Chemical Property of (2S,3S,4S,5S)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid

Chemical Property:

• Vapor Pressure: 1.49E-14mmHg at 25°C
• Boiling Point: 553.4°C at 760 mmHg
• PKA: 3.30±0.35(Predicted)
• Flash Point: 302.6°C
• PSA: 135.29000
• Density: 1.748g/cm³
• LogP: -3.28650
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 194.04265265
• Heavy Atom Count: 13
• Complexity: 191

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2S,3S,4S,5S)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid

There total 18 articles about (2S,3S,4S,5S)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid 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:

1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone (20513-98-8) → D-galacturonic acid (576-37-4,685-73-4,1986-14-7,1986-15-8,2073-35-0,3402-98-0,6556-12-3,6814-36-4,14982-50-4,15769-56-9,21675-50-3,21675-51-4,21675-52-5,21675-53-6,27766-62-7,28223-51-0,28223-52-1,39737-41-2,70332-45-5,84710-57-6,102681-51-6,108729-78-8,25249-06-3,25990-10-7,36562-70-6,36655-86-4)

Guidance literature:

With acidic cationen-exchanger; water;

DOI:10.1021/ja01614a072

Reference yield:

[GlcA-Rha]20[IdoA-Rha]6[GlcA-Rha-Xyl]6GlcA26Glc4[SO3-]30 → D-xylose (58-86-6) + L-Rhamnose (3615-41-6,478518-52-4) + D-glucose (50-99-7) + D-Glucuronic acid (6556-12-3,25249-06-3,25990-10-7,36562-70-6,36655-86-4) + D-galacturonic acid (576-37-4,685-73-4,1986-14-7,1986-15-8,2073-35-0,3402-98-0,6556-12-3,6814-36-4,14982-50-4,15769-56-9,21675-50-3,21675-51-4,21675-52-5,21675-53-6,27766-62-7,28223-51-0,28223-52-1,39737-41-2,70332-45-5,84710-57-6,102681-51-6,108729-78-8,25249-06-3,25990-10-7,36562-70-6,36655-86-4)

Guidance literature:

[GlcA-Rha]20[IdoA-Rha]6[GlcA-Rha-Xyl]6GlcA₂₆Glc₄[SO₃-]30; With water; trifluoroacetic acid; at 120 ℃; for 0.75h;

With Helix pomatia β-glucuronidase; at 37 ℃; for 16h; pH=5; aq. acetate buffer; Enzymatic reaction;

DOI:10.1016/j.carbpol.2011.12.041

Reference yield:

[GlcA-Rha]25[IdoA-Rha]6[GlcA-Rha-Xyl]4GlcA24Glc2[SO3-]32 → D-xylose (58-86-6) + L-Rhamnose (3615-41-6,478518-52-4) + D-glucose (50-99-7) + D-Glucuronic acid (6556-12-3,25249-06-3,25990-10-7,36562-70-6,36655-86-4) + D-galacturonic acid (576-37-4,685-73-4,1986-14-7,1986-15-8,2073-35-0,3402-98-0,6556-12-3,6814-36-4,14982-50-4,15769-56-9,21675-50-3,21675-51-4,21675-52-5,21675-53-6,27766-62-7,28223-51-0,28223-52-1,39737-41-2,70332-45-5,84710-57-6,102681-51-6,108729-78-8,25249-06-3,25990-10-7,36562-70-6,36655-86-4)

Guidance literature:

[GlcA-Rha]25[IdoA-Rha]6[GlcA-Rha-Xyl]4GlcA₂₄Glc₂[SO₃-]32; With water; trifluoroacetic acid; at 120 ℃; for 0.75h;

With Helix pomatia β-glucuronidase; at 37 ℃; for 16h; pH=5; aq. acetate buffer; Enzymatic reaction;

DOI:10.1016/j.carbpol.2011.12.041

upstream raw materials:

1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone

Nerol

D-myo-inositol

D-glucose

Downstream raw materials:

O²,O³,O⁴-triacetyl-O¹-((S)-1-benzyl-propyl)-β-D-glucopyranuronic acid methyl ester

O²,O³,O⁴-triacetyl-O¹-((S)-1-phenyl-butyl)-β-D-glucopyranuronic acid methyl ester

O¹-((1R)-trans-1-acetoxy-1,2-dihydro-[2]naphthyl)-O²,O³,O⁴-triacetyl-β-D-glucopyranuronic acid methyl ester

D-glycero-D-gulo-heptaric acid

Refernces