(2R,3R,3aR,6R,6aR)-2,3,6-trihydroxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one

Base Information

• Chemical Name: (2R,3R,3aR,6R,6aR)-2,3,6-trihydroxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one
• CAS No.: 32449-92-6
• Deprecated CAS: 3428-13-5,4214-08-8,6814-06-8
• Molecular Formula: C6H8O6
• Molecular Weight: 176.126
• Hs Code.: 29322980
• DSSTox Substance ID: DTXSID6041844
• Wikidata: Q76145881
• ChEMBL ID: CHEMBL3184229
• Mol file: 32449-92-6.mol

Synonyms:DTXSID6041844;D-Glucurone;DTXCID4021844;CAS-32449-92-6;D-(+)-Glucurono-3,6-lactone;NCGC00164524-01;Glucofuranurono-6,3-lactone;CHEMBL3184229;Tox21_113164;Tox21_300949;AKOS024286210;(2R,3R,3aR,6R,6aR)-2,3,6-trihydroxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one;NCGC00248224-01;NCGC00254851-01;Glucuronolactone;D(+)-Glucurono-3,6-lactone;(3R,3aR,5R,6R,6aR)-3,5,6-trihydroxytetrahydrofuro[3,2-b]furan-2(5H)-one

Chemical Property of (2R,3R,3aR,6R,6aR)-2,3,6-trihydroxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one

Chemical Property:

• Appearance/Colour: white crystals or crystalline powder
• Vapor Pressure: 1.31E-11mmHg at 25°C
• Melting Point: 172-175 °C(lit.)
• Refractive Index: 18.5 ° (C=5, H2O)
• Boiling Point: 403.5 °C at 760 mmHg
• PKA: 11.96±0.60(Predicted)
• Flash Point: 174.9 °C
• PSA: 104.06000
• Density: 1.749 g/cm³
• LogP: -2.80660
• Storage Temp.: Store at RT.
• Solubility.: water: soluble25mg/mL, clear, colorless
• Water Solubility.: SOLUBLE
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 176.03208797
• Heavy Atom Count: 12
• Complexity: 216

Purity/Quality:

100% ^*data from raw suppliers

D-Glucuronolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1(C2C(C(C(=O)O2)O)OC1O)O
• Isomeric SMILES: [C@H]1([C@@H]2[C@@H]([C@H](C(=O)O2)O)O[C@H]1O)O
• Uses: D-Glucurone is a glucuronic acid derivative. It is used for treating canine hepatitis. D-Glucurono-6,3-lactone is a glucuronic acid derivative studied for its effectiveness against canine hepatitis. It is utilized in the studies such as starting regent in the synthesis of 2,3,4,-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester, required for the preparation of 1-O-acyl glucuronide of the anti-inflammatory drug ML-3000, synthesis of optically active glucopyranoses, synthesis of long-chain alkyl glucofuranosides.

Technology Process of (2R,3R,3aR,6R,6aR)-2,3,6-trihydroxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one

There total 24 articles about (2R,3R,3aR,6R,6aR)-2,3,6-trihydroxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one 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: 5.0%

D-glucuronic acid (6556-12-3,489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + benzyl bromide (100-39-0) → D-glucuronic acid benzyl ester + (2S,3S,4S,5R,6R)-benzyl 3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylate + D-glucurono-6,3-lactone (32449-92-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.tet.2007.05.050

Reference yield:

3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-22-O-α-L-rhamnopyranosyl-squasapogenol → L-Rhamnose (3615-41-6,478518-52-4) + D-glucurono-6,3-lactone (32449-92-6)

Guidance literature:

With water; trifluoroacetic acid; for 2h; Reflux;

DOI:10.1248/cpb.c18-00881

Reference yield:

3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl-macedonic acid → L-Rhamnose (3615-41-6,478518-52-4) + D-glucurono-6,3-lactone (32449-92-6)

Guidance literature:

With water; trifluoroacetic acid; for 2h; Reflux;

DOI:10.1248/cpb.c18-00881

upstream raw materials:

D-Glucuronic acid

D-glucaric acid

D-myo-inositol

methyl beta-D-glucopyranoside

Downstream raw materials:

glucuronic acid methyl ester

1-(4-nitro-anilino)-1-deoxy-ξ-D-glucofuranuronic acid-3-lactone

D-Glucuronic acid

D-glucurono-3,6-lactone acetonide

Refernces

• 1、 Graefe. "-". . p. 205,208. Retrieved 1953.
• 2、 Hayashi, Hiroaki,Yokoshima, Keiko,Chiba, Ren,Fujii, Isao,Fattokhov, Inoyat,Saidov, Madibron. "Field survey of glycyrrhiza plants in Central Asia (5). Chemical characterization of G. Bucharica Collected in Tajikistan". . p. 534 - 539. Retrieved 2019/07/22.
• 3、 Bowkett, Elizabeth R.,Harding, John R.,Maggs, James L.,Park, B. Kevin,Perrie, Jennifer A.,Stachulski, Andrew V.. "Efficient synthesis of 1β-O-acyl glucuronides via selective acylation of allyl or benzyl d-glucuronate". . p. 7596 - 7605. Retrieved 2008/02/08.