211861-00-6

Basic information

• Product Name: (S,S) thréo e.e. 90% (+ 40% érythro)
• Synonyms: (S,S) thréo e.e. 90% (+ 40% érythro)
• CAS NO: 211861-00-6
• Molecular Weight: 282.423
• Mol File: 211861-00-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S,S) thréo e.e. 90% (+ 40% érythro)(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S) thréo e.e. 90% (+ 40% érythro)(211861-00-6)
• EPA Substance Registry System: (S,S) thréo e.e. 90% (+ 40% érythro)(211861-00-6)

Safety Data

• Hazardous Substances Data: 211861-00-6(Hazardous Substances Data)

Upstream product

• 6064-48-8 1-hydroxy-2(E)-pentadecene 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 10486-19-8 tridecanal 

Relevant articles and documents

Highly enantioselective aldol reaction with 2-trimethylsilyloxyfuran: The first catalytic asymmetric autoinductive aldol reaction

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Acetogenins of annonaceae. Part 86: Synthesis of a highly functionalized precursor of (-)-4-deoxygigantecin, an annonaceous acetogenin

A highly functionalized precursor of (-)-4-deoxygigantecin possessing six stereogenic centers has been prepared in 14 steps from tridecanal. The key steps are (i) enantioselective aldolization, (ii) diastereoselective C- glycosylation and (iii) diastereoselective aldolization reactions, all of them using 2-trimethylsilyloxyfuran as nucleophile. This strategy would allow us to prepare squamostatin D as well, another acetogenin of Annonaceae possessing two nonadjacent tetrahydrofuran rings and a closely related tetrahydrofuran pattern.

Highly Enantioselective 1,2-Addition of 2-[(Trimethylsilyl)oxy]furan to Aldehydes: Application to Muricatacin Synthesis

TMSOF 2-[(trimethylsilyl)oxy]furan has been used in an enantioselective aldol reaction for the first time. Indeed, addition of TMSOF to achiral aldehydes, in the presence (R)-1,1-bi-2-naphthol (Binol), gave the corresponding butenolides with moderate diastereomeric ratios (dr = 60%) and ee's between 60 and 90%. Application of this reaction to the total synthesis of annonaceous muricatacin in only two steps (in regards to the numerous multistep syntheses published so far) illustrated the efficiency of this strategy.