Diprogulic Acid

Base Information

• Chemical Name: Diprogulic Acid
• CAS No.: 18467-77-1
• Deprecated CAS: 129607-69-8,131400-21-0,136881-53-3,26996-98-5,27708-72-1,28300-95-0,36058-05-6,3768-13-6,49813-52-7,59795-40-3,64040-42-2,72349-14-5,56225-64-0,56288-61-0,1253699-69-2,1671061-51-0,1253699-69-2,136881-53-3,26996-98-5,27708-72-1,28300-95-0,3768-13-6,49813-52-7,56225-64-0,56288-61-0,59795-40-3,64040-42-2,72349-14-5
• Molecular Formula: C12H18 O7
• Molecular Weight: 274.271
• Hs Code.: 29329990
• European Community (EC) Number: 242-348-8
• UNII: 3981541LXD
• DSSTox Substance ID: DTXSID0047454
• Nikkaji Number: J41.419K
• Wikipedia: Diprogulic_acid
• Wikidata: Q3027939
• NCI Thesaurus Code: C65432
• ChEMBL ID: CHEMBL2110720
• Mol file: 18467-77-1.mol

Synonyms:Diprogulic Acid;Dikegulac;18467-77-1;Diprogulic acid [INN];Acido diprogulico;Acide diprogulique;Acidum diprogulicum;Dikegulac [ISO];DTXSID0047454;UNII-3981541LXD;Acide diprogulique [INN-French];Acido diprogulico [INN-Spanish];Acidum diprogulicum [INN-Latin];CHEBI:81986;Diacetone-2-keto-1-gulonic acid;EINECS 242-348-8;3981541LXD;(-)-2,3:4,6-Di-O-isopropylidene-2-keto-L-gulonic Acid;2,3:4,6-Di-O-isopropylidene-alpha-L-xylo-hexulofuranosonic acid;2,3:4,6-Diacetone-2-keto-L-gulonic acid;(-)-2,3:4,6-Di-O-isopropylidene-alpha-L-xylo-2-hexulofuranosonic Acid;oxogulonic acid diacetonide;2,3,4,6-di-O-Isopropylidene-alpha-L-xylo-2-hexulofuranosonic acid;alpha-L-xylo-2-Hexulofuranosonic acid, 2,3:4,6-bis-O-(1-methylethylidene)-;alpha-2,3:4,6-di-O-isopropylidene-L-xylo-hexulofuranosonic acid;2,3:4,6-Bis-O-(1-methylethyl-idene)alpha-L-xylo-2-hexulofuranosonic acid;.alpha.-L-xylo-2-Hexulofuranosonic acid, 2,3:4,6-bis-O-(1-methylethylidene)-, monohydrate;2,3,4,6-bis-O-(1-Methylethylidene)-alpha-L-xylo-2-hexulofuranosonic acid (9CI);Dikegulac [BSI:ISO];DIKEGULAC [MI];Diaceton-2-keto-L-gulonsaure;SCHEMBL120792;CHEMBL2110720;DTXCID8027454;(1R,2S,6R,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane-6-carboxylic acid;Tox21_300935;AKOS015955669;NCGC00166284-02;NCGC00254837-01;CAS-18467-77-1;C18825;Q3027939;2,3,4,6-bis-O-(1-Methylethylidene)-alpha-L-xylo-2-hexulofuranosonic acid;2,3:4,6-DI-O-ISOPROPYLIDENE-.ALPHA.-L-XYLO-HEXULOFURANOSONIC ACID

Chemical Property of Diprogulic Acid

Chemical Property:

• Vapor Pressure: 1.16E-06mmHg at 25°C
• Melting Point: 88-90 ºC(lit.)
• Refractive Index: 1.482
• Boiling Point: 375.2°Cat760mmHg
• Flash Point: 140°C
• PSA: 101.91000
• Density: 1.281g/cm³
• LogP: 0.34050
• Storage Temp.: 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 274.10525291
• Heavy Atom Count: 19
• Complexity: 418

Purity/Quality:

99% ^*data from raw suppliers

DIKEGULAC 98.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Useful:

• Canonical SMILES: CC1(OCC2C(O1)C3C(O2)(OC(O3)(C)C)C(=O)O)C
• Isomeric SMILES: CC1(OC[C@H]2[C@@H](O1)[C@H]3[C@@](O2)(OC(O3)(C)C)C(=O)O)C

Technology Process of Diprogulic Acid

There total 4 articles about Diprogulic 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: 1.8%

2,3:4,6-bis-O-isopropylidene-L-sorbose (17682-70-1) → dikegulac (18467-77-1) + (3aS,3bR,7aS,8aR)-2,2,5,5-Tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine-8a-carboxylic acid (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-8a-ylmethyl ester (52508-19-7)

Guidance literature:

With ruthenium(IV) oxide; sodium hydrogencarbonate; sodium chloride; In tetrachloromethane; water; Ambient temperature; electrooxidation;

DOI:10.1021/jo00352a006

Reference yield:

→ dikegulac (18467-77-1)

Guidance literature:

With potassium hydroxide; potassium chromate; Electrolysis_.Kupfer-Anode;

Reference yield:

2,3:4,6-bis-O-isopropylidene-L-sorbose (17682-70-1) → dikegulac (18467-77-1)

Guidance literature:

With oxygen; sodium carbonate; platinum on activated charcoal; In water; at 100 ℃; under 150.01 Torr; Mechanism; Rate constant;

upstream raw materials:

2,3:4,6-bis-O-isopropylidene-L-sorbose

Downstream raw materials:

(4S)-3,3-diethyl-4-{4-[(4-methylpiperazinyl)-carbonyl]phenoxy}azetidin-2-one

2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid potassium salt

Refernces

• 1、 -. "Crop-selective herbicide". . . Retrieved 2008/06/13.
• 2、 Torii, Sigeru,Inokuchi, Tsutomu,Sugiura, Toyoyuki. "Indirect Electrooxidation of Alkohols and Aldehydes by Using a Double Mediatory System Consisting of RuO4/RuO2 and Cl+/Cl- Redoxes in an Aqueous-Organic Two-Phase System". . p. 155 - 161. Retrieved 2007/10/02.