1,2-O-Cyclohexylidene-alpha-D-glucofuranose

Base Information

• Chemical Name: 1,2-O-Cyclohexylidene-alpha-D-glucofuranose
• CAS No.: 16832-21-6
• Molecular Formula: C12H20O6
• Molecular Weight: 260.287
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID80369228
• Nikkaji Number: J82.557C
• Wikidata: Q82156269
• Mol file: 16832-21-6.mol

Synonyms:16832-21-6;1,2-O-Cyclohexylidene-alpha-D-glucofuranose;(R)-1-((3a'R,5'R,6'S,6a'R)-6'-Hydroxytetrahydrospiro[cyclohexane-1,2'-furo[2,3-d][1,3]dioxol]-5'-yl)ethane-1,2-diol;(1R)-1-[(3aR,5R,6S,6aR)-6-hydroxyspiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-5-yl]ethane-1,2-diol;1,2-O-CYCLOHEXYLIDENE-a-D-GLUCOFURANOSE;DTXSID80369228;KAUCUKASFLXURN-RCZSTQMZSA-N;AKOS016007906;a-D-Glucofuranose,1,2-O-cyclohexylidene-;1,2-O-Cyclohexylidene- alpha -D-glucofuranose;1-O,2-O-Cyclohexylidene-alpha-D-glucofuranose;1,2-O-Cyclohexylidene-alpha-D-glucofuranose, 95%;1,2-O-Cyclohexane-1,1-diyl-alpha-D-xylo-hexofuranose;(1R)-1-[(3'AR,5'R,6'S,6'AR)-6'-HYDROXY-TETRAHYDROSPIRO[CYCLOHEXANE-1,2'-FURO[2,3-D][1,3]DIOXOL]-5'-YL]ETHANE-1,2-DIOL;(R)-1-((3a'R,5'R,6'S,6a'R)-6'-hydroxytetrahydrospiro[cyclohexane-1,2'-furo[3,2-d][1,3]dioxole]-5'-yl)ethane-1,2-diol

Chemical Property of 1,2-O-Cyclohexylidene-alpha-D-glucofuranose

Chemical Property:

• Appearance/Colour: white needles
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 163-168 °C(lit.)
• Refractive Index: 1.575
• Boiling Point: 499.9 °C at 760 mmHg
• Flash Point: 256.1 °C
• Density: 1.4g/cm³
• Storage Temp.: 2-8°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 260.12598835
• Heavy Atom Count: 18
• Complexity: 303

Purity/Quality:

97% ^*data from raw suppliers

1,2-O-Cyclohexylidene-a-D-glucofuranose ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2(CC1)OC3C(C(OC3O2)C(CO)O)O
• Isomeric SMILES: C1CCC2(CC1)O[C@@H]3[C@H]([C@H](O[C@@H]3O2)[C@@H](CO)O)O

Technology Process of 1,2-O-Cyclohexylidene-alpha-D-glucofuranose

There total 4 articles about 1,2-O-Cyclohexylidene-alpha-D-glucofuranose 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%

1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose (23397-76-4) → 1,2-O-cyclohexylidene-α-D-glucofuranose (16832-21-6)

Guidance literature:

With sodium dodecyl-sulfate; benzyl bromide; In water; at 20 ℃; Reagent/catalyst; chemoselective reaction;

DOI:10.1021/acs.joc.9b02561

Reference yield:

D-glucose (50-99-7) → 1,2-O-cyclohexylidene-α-D-glucofuranose (16832-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1: concentrated sulfuric acid

2: hydrogen chloride; methanol

With hydrogenchloride; methanol; sulfuric acid;

DOI:10.1021/ja01177a036

Reference yield:

D-glucose (50-99-7) → 1,2-O-cyclohexylidene-α-D-glucofuranose (16832-21-6) + 1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose (23397-76-4)

Guidance literature:

With sulfuric acid; cyclohexanone;

upstream raw materials:

D-glucose

1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose

Downstream raw materials:

4,5-cyclohexylidenedioxy-3-hydroxytetrahydrofuran-2-carbaldehyde

O³,O⁵,O⁶-Tribenzoyl-D-glucose

C₂₇H₃₂O₆

1,2-dioxaspiro[2,5]octane-3-deoxy-3-[(3-chlorobenzyl)amido]-5,6-O-isopropylidene-α-D-allofuranoside