287483-43-6

Basic information

• Product Name: (2E)(5S,6S)-5-(tert-butyldiphenylsilanyloxy)-undec-2-ene-1,6-diol
• Synonyms: (2E)(5S,6S)-5-(tert-butyldiphenylsilanyloxy)-undec-2-ene-1,6-diol
• CAS NO: 287483-43-6
• Molecular Weight: 440.698
• Mol File: 287483-43-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2E)(5S,6S)-5-(tert-butyldiphenylsilanyloxy)-undec-2-ene-1,6-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)(5S,6S)-5-(tert-butyldiphenylsilanyloxy)-undec-2-ene-1,6-diol(287483-43-6)
• EPA Substance Registry System: (2E)(5S,6S)-5-(tert-butyldiphenylsilanyloxy)-undec-2-ene-1,6-diol(287483-43-6)

Safety Data

• Hazardous Substances Data: 287483-43-6(Hazardous Substances Data)

Upstream product

• 111-71-7 heptanal 
• 287483-41-4 (4S,5S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyldihydrofuran-2-one 
• 165605-79-8 (4S,5S)-4,5-dihydro-4-hydroxy-5-pentyl-2-(3H)-furanone 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 36781-67-6 methyl (trans-3-nonenoate) 
• 28163-88-4 (E)-non-3-enoic acid 
• 329010-29-9 ethyl (2E)(5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-hydroxydec-2-enoate 
• 287483-42-5 (E)-(5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-undec-2-enoic acid methyl ester 

Downstream Products

• 287483-47-0 tert-butyl-[5-((2R)-oxiran-2-yl)-2-(2S,3S,5R)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane 
• 287483-50-5 tert-butyl-[5-((2S)-oxiran-2-yl)-2-(2S,3S,5S)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane 
• 287483-51-6 (1S)-1-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-dec-9-en-1-ol 
• 287483-48-1 (1R)-1-[(4S,5S,2R)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-dec-9-en-1-ol 
• 287483-49-2 (2R)-2-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-2-methanesulfonyloxy-ethyl benzoate 
• 287483-46-9 (2S)-2-[(4S,5S,2R)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-2-methanesulfonyloxy-ethyl benzoate 
• 1053616-72-0 Benzoic acid (S)-2-[(2R,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-pentyl-tetrahydro-furan-2-yl]-2-hydroxy-ethyl ester 
• 287483-45-8 (1R)-1-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-ethane-1,2-diol 
• 287483-44-7 (1S)-1-[(4S,5S,2R)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-ethane-1,2-diol 

Relevant articles and documents

β-hydroxy-γ-lactones as chiral building blocks for the enantioselective synthesis of marine natural products

The enantioselective synthesis of trans-(+)-laurediol, (2S,3S,5R)-5-[(1R)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol, and (2S,3S,5S)-5-[(1S)-1-hydroxy-9-decenyl]-2-pentyltetrahydro-3-furanol are described. In addition, a formal synthesis of trans-(-)-kumausyne is also developed. All the synthetic procedures have in common the use of enantiomerically enriched β-hydroxy-γ-lactones, easily available by Sharpless asymmetric dihydroxylation (AD) from the suitable β,γ-unsaturated ester. The use of Katsuki - Sharpless asymmetric epoxidation (AE) as an additional enantioselective reaction provides cyclic compounds of high enantiomeric purity.