78008-36-3

Basic information

• Product Name: (R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde
• Synonyms: (R)-1,4-DIOXASPIRO[4.5]DECANE-2-CARBOXALDEHYDE;(+)-1,4-DIOXOSPIRO[4,5]DECANE-2-CARBOXALDEHYDE;(+)-1,4-DIOXOSPIRO[4,5]DECANE-2-CARBOXYALDEHYDE;(R)-(+)-1,4-Dioxospiro(4,5)decane-2-carboxaldehyde;(+)-1,4-DIOXOSPIRO[4,5]DECANE-2-CABOXYALDEHYDE;1,4-DIOXASPIRO[4.5]DECANE-2-CARBOXALDEHYDE;(R)-(+)-2,2,CYCLOHEXYL-1,3-DIOXALANE-4-CARBOXALDEHYDE;(R)-1,4-Dioxaspiro[4
• CAS NO: 78008-36-3
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.21
• Product Categories: Small molecule;chiral;Aldehydes;Chiral Building Blocks;Organic Building Blocks
• Mol File: 78008-36-3.mol
• Article Data: 43

Chemical Properties

• Boiling Point: 271.195°C at 760 mmHg
• Flash Point: 218 °F
• Appearance: /
• Density: 1.108 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: n20/D 1.472(lit.)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: (R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde(78008-36-3)
• EPA Substance Registry System: (R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde(78008-36-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 78008-36-3(Hazardous Substances Data)

Usage

Uses

Reactant for:Proline-catalyzed Diels Alder reactionStereodivergent synthesis of carbahexofuranoses employing a Wittig olefination-Claisen rearrangement protocolWittig reactionsCrotylation reactionsAsymmetric synthesis of Goniothalesdiol A via stereocontrolled allylation and base-catalyzed oxy-Michael addition

InChI:InChI=1/C9H14O3/c10-6-8-7-11-9(12-8)4-2-1-3-5-9/h6,8H,1-5,7H2/t8-/m0/s1

Upstream product

• 76779-67-4 1,2,5,6-di-O-cyclohexylidene-D-mannitol 
• 95335-91-4 (S)-1,4-dioxaspiro<4.5>decane-2-methanol 
• 933-40-4 cycloxexanone dimethyl ketal 
• 69-65-8 mannitol 
• 108-94-1 cyclohexanone 
• 6614-52-4 5,6-O-cycloheyxlidene-(L)-ascorbic acid 
• 99744-80-6 4,5-O-cyclohexylidene-L-arabinose dibenzyl dithioacetal 
• 229639-27-4 (S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-ethane-1,2-diol 
• 102335-37-5 5-((2S)-1,4-dioxaspiro[4.5]dec-2-yl)(3S,4R,5S)-3,4-dihydroxy-3,4,5-trihydrofuran-2-one 
• 229639-21-8 3,4-O-cyclohexylidene-L-(S)-erythrulose 
• 881377-27-1 5,6-O-cyclohexylidene-gulono-1,4-lactone 
• 103959-91-7 (S)-2-(benzyloxy)-2-{(S)-1',4'-dioxaspiro[4.5]decan-2'-yl}ethan-1-ol 

Downstream Products

• 137734-20-4 (S)-4-Benzyloxy-5-((R)-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-triethylsilanyloxy-methyl)-5H-furan-2-one 
• 137734-21-5 (R)-4-Benzyloxy-5-((R)-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-triethylsilanyloxy-methyl)-5H-furan-2-one 
• 137734-31-7 (S)-4-Benzyloxy-5-((R)-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-hydroxy-methyl)-5H-furan-2-one 
• 137734-38-4 (R)-4-Benzyloxy-5-((R)-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-hydroxy-methyl)-5H-furan-2-one 
• 134678-18-5 (1S,2R)-1-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-2-methoxy-2-phenylsulfanyl-ethanol 
• 134592-29-3 (1S,2S)-1-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-2-methoxy-2-phenylsulfanyl-ethanol 
• 134592-26-0 (R)-1-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-2-methoxy-2-phenylsulfanyl-ethanone 
• 134592-25-9 (S)-1-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-2-methoxy-2-phenylsulfanyl-ethanone 
• 118878-30-1 (E)-(S)-4-Methylsulfanyl-4-(toluene-4-sulfonyl)-but-3-ene-1,2-diol 
• 136935-39-2 2-[(Z)-(S)-2-(1,4-Dioxa-spiro[4.5]dec-2-yl)-vinyl]-benzoic acid methyl ester 
• 136935-40-5 2-[(E)-(S)-2-(1,4-Dioxa-spiro[4.5]dec-2-yl)-vinyl]-benzoic acid methyl ester 
• 137734-33-9 (S)-4-Benzyloxymethoxy-5-((R)-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-hydroxy-methyl)-5H-furan-2-one 
• 137734-36-2 (R)-4-Benzyloxymethoxy-5-((R)-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-hydroxy-methyl)-5H-furan-2-one 
• 116185-65-0 (1R,2R,S,4R)-5-(benzyloxy)-1-(2,2-pentamethylene-1,3-dioxolan-4-yl)-4-methylpentan-2-ol 

Relevant articles and documents

Synthesis of enantiomeric diethyl (1R,2R)- and (1S,2R)-1,2,3- trihydroxypropylphosphonates

Addition of diethyl phosphite to 2,3-O-cyclohexylidene-D-glyceraldehyde catalyzed by triethylamine or fluorides led to ca. 35:65 mixtures of diethyl (1R,2R)- and (1S,2R)-2,3-O-cyclohexytidene-1,2,3-trihydroxypropylphosphonates (4a) and (4b). Application of lithium diethylphosphonate only slightly improved diastereoselectivity. Through chromatographic separation of 4a and 4b the protected trihydroxypropylphosphonates became available for the first time as pure enantiomers. The 1S configuration in the major diastereoisomer 4b was assigned on the basis of conformational and configurational analysis of 1,2-O-isopropylidene derivatives obtained from the title compounds.

An efficient synthesis of enantiomerically pure diethyl 2,3-dihydroxypropylphosphonate

A reliable method for the synthesis of the enantiomerically pure diethyl (R)-2,3-dihydroxypropylphosphonate from 1,2;5,6-di-O-cyclohexylidene-D-mannitol is elaborated.

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.

Enantiodivergent syntheses of (+)- and (?)-1-(2,6-dimethylphenoxy)propan-2-ol: A way to access (+)- and (?)-mexiletine from D-(+)-mannitol

Chiron approach was used to acquire optically pure (R)- and (S)-1-(2,6-dimethylphenoxy)propan-2-ol, immediate precursors of (S)- and (R)-mexiletines, respectively. Two different routes were followed from a D-mannitol-derived optically pure common precursor to get the enantiomeric alcohols separately. Comparison of their specific rotation values with the corresponding literature values as well as exact mirror-image relationship between their CD curves proved their high enantiopurity. These alcohols were then transformed to the corresponding amine-drugs in an efficient one-step process instead of two steps described in the literature.