(-)-2,3-Cyclohexylidene-L-erthuronic acid

Base Information

• Chemical Name: (-)-2,3-Cyclohexylidene-L-erthuronic acid
• CAS No.: 85029-84-1
• Molecular Formula: C10H14 O5
• Molecular Weight: 214.218
• Hs Code.: 2932999099
• UNII: 8HP7NQG8K6
• Nikkaji Number: J309.593B
• Mol file: 85029-84-1.mol

Synonyms:85281-85-2;(-)-2,3-Cyclohexylidene-L-erthuronic acid;(+)-2,3-Cyclohexylidene-L-erythruronic acid;2,3-O-CYCLOHEXYLIDENE-L(-)-ERYTHRURONOLACTONE;8HP7NQG8K6;SCHEMBL20869760;4-hydroxyspiro[6aH-furo[3,4-d][1,3]dioxole-2,1'-cyclohexane]-6-one;6-hydroxyspiro[6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-one;FT-0604410;FT-0675559;4'-hydroxydihydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxol]-6'(6a'H)-one;4-hydroxyspiro[4,6a-dihydro-3aH-furo[4,3-d][1,3]dioxole-2,1'-cyclohexane]-6-one;6,6a-Dihydro-6-hydroxyspiro[furo[3,4-d][1,3]dioxole-2,1'-cyclohexan]-4(3aH)-one;Spiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxol]-4'(3'aH)-one, dihydro-6'-hydroxy-;Spiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxol]-4'(3'aH)-one, dihydro-6'-hydroxy-, (3'aR,6'R,6'aS)-

Chemical Property of (-)-2,3-Cyclohexylidene-L-erthuronic acid

Chemical Property:

• Boiling Point: 438.6oC at 760 mmHg
• Flash Point: 179.6oC
• PSA: 64.99000
• Density: 1.39g/cm3
• LogP: 1.34610
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 214.08412354
• Heavy Atom Count: 15
• Complexity: 284

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2(CC1)OC3C(O2)C(=O)OC3O

Technology Process of (-)-2,3-Cyclohexylidene-L-erthuronic acid

There total 3 articles about (-)-2,3-Cyclohexylidene-L-erthuronic 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: 88.0%

2,3-O-cyclohexylidene-D-gulonic acid γ-lactone (111005-66-4,128165-51-5) → (2R,3S,4RS)-2,3-(cyclohexylidenedioxy)-4-oxo-4-butanoic acid γ-lactone (85029-84-1)

Guidance literature:

With sodium hydroxide; sodium periodate;

DOI:10.1021/jo00302a043

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (2R,3S,4RS)-2,3-(cyclohexylidenedioxy)-4-oxo-4-butanoic acid γ-lactone (85029-84-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / dowex 50W (H⁺) / benzene / 6 h / Heating

2: 51 percent / aq. EtOH, dowex 50W (H⁺) / 16 h / 45 °C

3: 88 percent / NaIO₄, aq.NaOH

With sodium hydroxide; sodium periodate; ethanol; Dowex 50W (H⁺); In benzene;

DOI:10.1021/jo00302a043

Reference yield:

2,3:5,6-di-O-cyclohexylidene-D-gulonic acid γ-lactone (40656-50-6,119680-72-7,119680-76-1) → (2R,3S,4RS)-2,3-(cyclohexylidenedioxy)-4-oxo-4-butanoic acid γ-lactone (85029-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / aq. EtOH, dowex 50W (H⁺) / 16 h / 45 °C

2: 88 percent / NaIO₄, aq.NaOH

With sodium hydroxide; sodium periodate; ethanol; Dowex 50W (H⁺);

DOI:10.1021/jo00302a043

upstream raw materials:

2,3-O-cyclohexylidene-D-gulonic acid γ-lactone

cyclohexanone

2,3:5,6-di-O-cyclohexylidene-D-gulonic acid γ-lactone

Refernces