110426-22-7

Upstream product

• 110426-21-6 (E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one 
• 70150-60-6 ethyl 2E-4-(benzyloxy)-2-butenoate 
• 60656-87-3 benzyloxyacetoaldehyde 
• 71516-48-8 2-((benzyloxy)methyl)-1,3-dioxolane 
• 100-51-6 benzyl alcohol 
• 20194-18-7 sodium phenyl-methanolate 

Downstream Products

• 110426-23-8 (2R,3R,4S)-1-Benzyloxy-5-((R)-toluene-4-sulfinyl)-pentane-2,3,4-triol 
• 205449-13-4 Methyl 5-O-tert-butyldiphenylsilyl-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate 
• 605668-78-8 4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane 
• 605668-79-9 4-[1-azido-2-benzyloxy-(1R)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane 
• 610316-26-2 [(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol 
• 610316-28-4 {1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl}-carbamic acid tert-butyl ester 
• 610316-27-3 [(4S,5S)-5-((R)-1-Azido-2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-diphenyl-silane 
• 610316-29-5 tert-butoxycarbonylamino-[5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid 
• 110426-23-8 (2S,3S,4R)-1-Benzyloxy-5-((R)-toluene-4-sulfinyl)-pentane-2,3,4-triol 
• 609811-92-9 (2S,3S,4R)-5-benzyloxy-4-bromo-1-(4-methylphenylsulfinyl)pentane-2,3-diol 
• 609812-03-5 tert-butyl (3E,1R,2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-carbamate 
• 609811-94-1 (1S)-1-[(3S)-3-(benzyloxymethyl)oxiran-2-yl]-2-(4-methylphenylsulfinyl)ethan-1-ol 
• 609811-93-0 (4S,5S)-4-[(1R)-2-benzyloxy-1-bromoethyl]-2,2-dimethyl-5-(4-methylphenylsulfinylmethyl)-1,3-dioxolane 
• 609811-95-2 (2S,3R,4R)-4-azido-5-benzyloxy-1-(4-methylphenylsulfinyl)pentane-2,3-diol 

Relevant academic research and scientific papers

Novel, short, stereospecific synthesis of lyxo-(2R,3R,4R)-phytosphingosine and erythro-(2R,3S)-sphingosine

lyxo-Phytosphingosine and erythro-sphingosine have been elaborated from a common intermediate. The key step in the reaction sequence involves stereo- and regiospecific functionalization of an olefin by intramolecular nucleophilic sulfinyl group participat

Novel, efficient and stereospecific synthesis of xylo-(2R,3S,4S)-phytosphingosine and threo-(2R,3R)-sphingosine

The stereo- and regioselective elaboration of a bromohydrin from an olefinic precursor and Pummerer ene reaction for carbon-carbon bond formation are the key steps in a novel and flexible synthesis of xylo-phytosphingosine and threo-sphingosine.

The sulfinyl moiety as an internal nucleophile. Part 8: Efficient, stereospecific synthesis of (+)-polyoxamic acid

A straightforward and stereospecific synthesis of (+)-polyoxamic acid is disclosed. The key step of the synthesis involves the regio- and stereospecific bromohydration of an olefin via intramolecular participation by the sulfinyl group.

ASYMMETRIC SYNTHESIS OF POLYHYDROLXYLATED NATURAL PRODUCTS I. EFFICIENT PREPARATION OF L-ARABINITOL

A new approach to sugar synthesis is demonstrated through the synthesis of L-arabinitol.Reduction of allylic β-ketosulfoxides followed by hydroxylation of the double bond in the resulting allylic β-ketosulfoxides are the two important asymmetric steps involved in the process.

Stereospecific hydroxylation of chiral allylic β-hydroxysulfoxides: asymmetric synthesis of L-arabinitol

Chiral allylic β-hydroxysulfoxides 2 have been hydroxylated by the osmium tetroxide catalyzed reaction.The reaction can be highly stereoselective depending on the nature of the substituent linked to the double bond and the configurations of the sulfoxide and hydroxylic groups.The diastereoselectivity can be as high as 90 percent.This methodology was applied to the asymmetric synthesis of L-arabinitol.