2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone

Base Information

• Chemical Name: 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone
• CAS No.: 14440-56-3
• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.271
• DSSTox Substance ID: DTXSID601231735
• Nikkaji Number: J81.773B
• Mol file: 14440-56-3.mol

Synonyms:Mannonicacid, 2,3:5,6-di-O-isopropylidene-, g-lactone (6CI,7CI); Mannonic acid, 2,3:5,6-di-O-isopropylidene-,g-lactone, D- (8CI);Furo[3,4-d]-1,3-dioxole, D-mannonic acid deriv.;2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone

Chemical Property of 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone

Chemical Property:

• PSA: 63.22000
• LogP: 0.58340
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 258.11033829
• Heavy Atom Count: 18
• Complexity: 377

Purity/Quality:

98%, ^*data from raw suppliers

2,3:5,6-Di-O-isopropylidene-D-mannonic acid-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)C2C3C(C(=O)O2)OC(O3)(C)C)C
• Isomeric SMILES: CC1(OC[C@@H](O1)[C@@H]2[C@H]3[C@@H](C(=O)O2)OC(O3)(C)C)C

Technology Process of 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone

There total 32 articles about 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone 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: 100.0%

2,3:5,6-Di-O-isopropylidene-1-(2-thiazolyl)-α-D-mannofuranose (160701-79-1) → 1,3-thiazole (288-47-1) + 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone (7306-64-1,14440-56-3,23262-80-8,27108-15-2,49561-21-9,67642-42-6)

Guidance literature:

With 4 A molecular sieve; In toluene; at 130 ℃; for 14h; Product distribution; Mechanism; elimination of thiazole from thiazolylketofuranoses and -ketopyranoses; no reaction with 1-O-acetyl and 1-O-trimethylsilyl derivatives, thiazolyl alcohols; no elimination of furyl- and thienyl-group;

DOI:10.3987/COM-98-8154

Reference yield: 100.0%

2,3,5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4) → 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone (7306-64-1,14440-56-3,23262-80-8,27108-15-2,49561-21-9,67642-42-6)

Guidance literature:

With iodine; potassium carbonate; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/j.tet.2013.05.021

Reference yield: 95.0%

2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (14131-84-1) → 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone (7306-64-1,14440-56-3,23262-80-8,27108-15-2,49561-21-9,67642-42-6)

Guidance literature:

With Dess-Martin periodane; tert-butyl alcohol; In dichloromethane; at 25 ℃;

upstream raw materials:

2,3,5,6-di-O-isopropylidene-D-mannofuranose

2,3;5,6-di-O-isopropylidene-β-D-mannofuranose

1-C-nitroso-2,3:5,6-di-O-isopropylidenemannofurasonyl chloride

cyclohexa-1,3-diene

Downstream raw materials:

(3aS,6S,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one O-benzyl-oxime

(R)-1-[(3aS,4R,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethane-1,2-diol

2,3:5,6-di-O-isopropylidene-α-D-mannofuranose

2,3:5,6-di-O-isopropylidene-1-C-phenyl-D-mannofuranoside

Refernces

• 1、 Sarabia-Garcia, Francisco,Lopez-Herrera, Fidel J.,Pino-Gonzalez, Maria S.. "A New Synthesis for 2-Deoxy-KDO, a Potent Inhibitor of CMP-KDO Synthetase.". . p. 6709 - 6712. Retrieved 1994.
• 2、 Tam, Tim Fat,Fraser-Reid, Bert. "Chiral Models of the Furenone Moiety of Germacranolide Sesquiterpenes". . p. 1344 - 1346. Retrieved 1980.
• 3、 Joseph, Cosam C,Regeling, Henk,Zwanenburg, Binne,Chittenden, Gordon J.F. "Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-D-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-D-glucitol)". . p. 6907 - 6911. Retrieved 2002.
• 4、 Zhao, Yachen,Wang, Shengyang,Yu, Biao. "Dimerization of aldosuloses and aldonolactones into branched higher carbon sugars". supporting information. p. 2020 - 2022. Retrieved 2020/02/22.