76779-67-4

Usage

Uses

Used in Asymmetric Synthesis:
1,2:5,6-Di-O-cyclohexylidene-D-mannitol is used as a chiral resolving agent for separating enantiomers and resolving racemic mixtures of compounds, which is essential in producing pure enantiomers for various applications.
Used in Pharmaceutical Industry:
1,2:5,6-Di-O-cyclohexylidene-D-mannitol is used as a reagent in the preparation of chiral ligands and catalysts for various chemical reactions, contributing to the development and production of chiral drugs and other bioactive compounds.

InChI:InChI=1/C18H30O6/c19-15(13-11-21-17(23-13)7-3-1-4-8-17)16(20)14-12-22-18(24-14)9-5-2-6-10-18/h13-16,19-20H,1-12H2/t13-,14?,15-,16-/m1/s1

Upstream product

• 69-65-8 mannitol 
• 1670-47-9 1,1-diethoxycyclohexane 
• 108-94-1 cyclohexanone 

Downstream Products

• 78008-36-3 (R)-2,3-cyclohexylideneglyceraldehyde 
• 870672-96-1 1,2:5,6-di-O-cyclohexylidene-3-O-phenylcarbamoyl-D-mannitol 
• 870672-95-0 1,2:5,6-di-O-cyclohexylidene-3-O-[(4-methyl)phenylcarbamoyl]-D-mannitol 
• 870672-94-9 1,2:5,6-di-O-cyclohexylidene-3-O-[(3,5-dimethyl)phenylcarbamoyl]-D-mannitol 
• 78008-36-3 (S)-cyclohexylidene glyceraldehyde 

Relevant academic research and scientific papers

Novel 1,2,3-triazole-tethered Pam3CAG conjugates as potential TLR-2 agonistic vaccine adjuvants

A focused library of water soluble 1,2,3-triazole tethered glycopeptide conjugates derived from variety of azido-monosaccharides and aliphatic azido-alcohols were synthesized through manipulation at the C-terminus of Pam3CAG and screened for their potential as TLR2 agonistic adjuvants against HBsAg antigen. In vitro ligand induced TLR2 signal activation was observed with all the analogues upon treatment with HEK blue TLR2 cell lines. Conjugate derived from ribose (6e), which exhibited pronounced HBsAg specific antibody (IgG) titer also shown enhanced CD8+ population indicating superior cell mediated immunity compared to standard adjuvant Pam3CSK4. Further, docking studies revealed ligand induced heterodimerization between TLR1 and 2. Overall, the result indicates the usefulness of novel conjugates as potential vaccine adjuvant.

Synthesis of ABBV-168, a 2′-Bromouridine for the Treatment of Hepatitis C

ABBV-168 is a dihalogenated nucleotide under investigation for the treatment of hepatitis C virus. Three synthetic routes aimed at achieving the stereoselective installation of the C2′ gem-Br,F substitution and subsequent Vorbruggen glycosylation were explored to prepare the penultimate nucleoside intermediate. Development culminated in a route to ABBV-168 featuring a de novo chromatography-free furanose synthesis, protecting group-directed Vorbruggen glycosylation, and highly selective phosphoramidation to furnish the API.

Total Synthesis and Stereochemical Revision of 4,8-Dihydroxy-3,4-dihydrovernoniyne

The first asymmetric total synthesis of two possible diastereomers (4S,5R)-4,8-dihydroxy-3,4-dihydrovernoniyne 5 and (4S,5S)-4,8-dihydroxy-3,4-dihydrovernoniyne 5a is accomplished. Salient features of the synthesis involve Cadiot-Chodkiewicz coupling and

Stereodivergent approach to Alzheimer's therapeutic agent (R)-(?) and (S)-(+)-arundic acid employing chiral 4-pentenol derivatives as building blocks

An efficient stereodivergent total synthesis of anti-Alzheimer agent (R)-(?) and (S)-(+)-arundic acid has been achieved from both chiral and nonchiral materials. This strategy features an efficient approach to separable diastereomeric C-2 chiral 4-pentenol intermediates employing proline catalysed asymmetric α-aminooxylation and [3,3] sigmatropic Claisen rearrangement are the highlights of present synthesis.

(R)-2,3-cyclohexylideneglyceraldehyde, a chiral pool synthon for the synthesis of 2-azido-1,3-diols

A new approach was proposed for the synthesis of 2-azido-1,3-diols from easily available and inexpensive chiral pool synthon (R)-2,3-O-cyclohexylidene-D-glyceraldehyde, through Mitsunobu azidation of 1,2-diols. Both C(2) and C(1) azides in variable ratios

A facile approach to chiral 1,4-benzodioxane toward the syntheses of doxazosin, prosympal, piperoxan, and dibozane

The process describes the concise synthesis of (R/S)-enantiomers of doxazosin, an antidepressant drug and α-adrenergic receptor antagonists like prosympal, piperoxan, and dibozane in practical yields from easily available (R)-2,3-O-cyclohexylidene-d-glyce

Synthesis of epothilones molecule fragment (15R)-C13-C 21 from D-mannitol

Efficient synthesis of an epothilone molecules fragment (15R)-C 13-C21 was carried out from D-mannitol through its conversion into methyl 2,3-O-cyclohexylidene-D-glycerate followed by the cyclopropanation of the ester group with ethy

A New Convenient Method for the Synthesis of Chiral C3-Synthons

Routes are described for the facile preparation of protected optically pure D- and L-glyceric acid (1a,b; 2a,b) starting from D-mannitol, D-isoascorbic acid and L-ascorbic acid.The key step is a ruthenium catalyzed oxidative cleavage of the vicinal diols 4a,b or the α-hydroxy acids 7a,b; 10a,b.

3-Alkylated (R)-2,3-Dihydroxyalkyl p-Toluenesulfonates - Homochiral Building Blocks for Modified Steroid Side Chains

Oxidative cleavage of 1,2:5,6-di-O-cyclohexylidene-D-mannitol (2) with lead(IV) acetate yields (R)-2,3-O-cyclohexylideneglyceraldehyde, which was transformed by oxidation and esterification into methyl 2,3-O-cyclohexylideneglycerate.Grignard reaction with