1269417-04-0

Basic information

• Product Name: 2-[(SS,2R)-2-chloro-2-deutero-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane
• Synonyms: 2-[(SS,2R)-2-chloro-2-deutero-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane
• CAS NO: 1269417-04-0
• Molecular Weight: 275.76
• Mol File: 1269417-04-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-[(SS,2R)-2-chloro-2-deutero-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(SS,2R)-2-chloro-2-deutero-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane(1269417-04-0)
• EPA Substance Registry System: 2-[(SS,2R)-2-chloro-2-deutero-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane(1269417-04-0)

Safety Data

• Hazardous Substances Data: 1269417-04-0(Hazardous Substances Data)

Upstream product

• 1269416-92-3 2-[2-(4-methylphenyl)thioethyl]-1,3-dioxolane 
• 1269416-93-4 2-[(SS)-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane 
• 1269416-94-5 2-[(SS,2S)-2-chloro-2-(4-methylphenyl)sulfinylethyl]-1,3-dioxolane 
• 120483-06-9 3-p-Tolylsulfanyl-propionaldehyde 
• 811-98-3 d⁽⁴⁾-methanol 
• 106-45-6 para-thiocresol 

Downstream Products

• 640-57-3 phenyltolylsulfone 
• 1269416-97-8 C₁₀H₁₁⁽²⁾HClNO₂ 
• 1269417-10-8 C₁₀H₁₁⁽²⁾HClNO₃ 
• 1269416-96-7 C₁₅H₁₈⁽²⁾H₂ClNO₅ 
• 16491-20-6 (R)-1-methyl-4-(phenylsulfinyl)benzene 
• 1269416-95-6 C₁₆H₂₂⁽²⁾HBClNO₄ 

Relevant articles and documents

Investigation of functionalized α-chloroalkyllithiums for a stereospecific reagent-controlled homologation approach to the analgesic alkaloid (-)-epibatidine

Four putative functionalized α-chloroakyllithiums RCH 2CHLiCl, where R=CHCH2 (18 a), CCH (18 b), CH 2OBn (18 c), and CH[O(CH2)2O] (18 d), were generated in situ by sulfoxide-lithium exchange from α-chlorosulfoxides, and investigated for the stereospecific reagent-controlled homologation (StReCH) of phenethyl and 2-chloropyrid-5-yl (17) pinacol boronic esters. Deuterium labeling experiments revealed that α-chloroalkyllithiums are quenched by proton transfer from their α-chlorosulfoxide precursors and it was established that this effect compromises the yield of StReCH reactions. Use of α-deuterated α-chlorosulfoxides was discovered to ameliorate the problem by retarding the rate of acid-base chemistry between the carbenoid and its precursor. Carbenoids 18 a and 18 b showed poor StReCH efficacy, particularly the propargyl group bearing carbenoid 18 b, the instability of which was attributed to a facile 1,2-hydride shift. By contrast, 18 d, a carbenoid that benefits from a stabilizing interaction between O and Li atoms gave good StReCH yields. Boronate 17 was chain extended by carbenoids 18 a, 18 b, and 18 d in 16, 0, and 68 % yield, respectively; α-deuterated isotopomers D-18 a and D-18 d gave yields of 33 and 79 % for the same reaction. Double StReCH of 17 was pursued to target contiguous stereodiads appropriate for the total synthesis of (-)-epibatidine (15). One-pot double StReCH of boronate 17 by two exposures to (S)-D-18 a (≤66 % ee), followed by work-up with KOOH, gave the expected stereodiad product in 16 % yield (d.r.～67:33). The comparable reaction using two exposures to (S)-D-18 d (≤90 % ee) delivered the expected bisacetal containing stereodiad (R,R)-DD-48 in 40 % yield (≥98 % ee, d.r.=85:15). Double StReCH of 17 using (S)-D-18 d (≤90 % ee) followed by (R)-D-18 d (≤90 % ee) likewise gave (R,S)-DD-48 in 49 % yield (≥97 % ee, d.r.=79:21). (R,S)-DD-48 was converted to a dideuterated isotopomer of a synthetic intermediate in Corey's synthesis of 15. Copyright