106820-48-8

Upstream product

• 5336-08-3 D-Ribono-1,4-lactone 
• 99315-75-0 (-)-5-O-(diphenyl-t-butylsilyl)-2,3-O-(thiocarbonyl)-D-ribono-1,4-lactone 
• 92512-33-9 (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one 
• 106731-86-6 (S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-dihydro-furan-2-one 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 56-86-0 L-glutamic acid 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 78508-96-0 (5S)-5-(hydroxymethyl)-5H-furan-2-one 
• 186581-53-3 diazomethane 
• 99315-76-1 (5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone 

Downstream Products

• 106820-55-7 (3aS,4S,6aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6a-methyl-3,3a,4,6a-tetrahydro-furo[3,4-c]pyrazol-6-one 
• 106820-53-5 (3R,4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-3,4-dimethyl-dihydro-furan-2-one 
• 106820-51-3 (3R,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-dihydro-furan-2-one 
• 106820-57-9 (3R,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-3,4-dimethyl-dihydro-furan-2-one 
• 106820-54-6 (3R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-4-methyl-dihydro-furan-2-one 
• 106820-56-8 (S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-5H-furan-2-one 
• 106820-52-4 (2R,3R,4S)-5-[(tert-butyldiphenylsilyl)oxy]-2-hydroxy-3-methyl-4-pentanolide 
• 106820-50-2 2,3-dideoxy-3-C-methyl-5-O-tert-butyldiphenylsilyl-D-threo-pentono-1,4-lactone 
• 206982-04-9 Benzoic acid (1R,2S)-2-carboxy-cyclopropylmethyl ester 
• 206982-03-8 Benzoic acid (1R,2S)-2-formyl-cyclopropylmethyl ester 
• 206982-02-7 Benzoic acid (1R,2R)-2-vinyl-cyclopropylmethyl ester 
• 157523-16-5 Toluene-4-sulfonic acid (1S,2S,5R)-4-oxo-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester 
• 157604-58-5 (1R,2S)-2-Formyl-cyclopropanecarboxylic acid methyl ester 
• 159950-58-0 (1R,4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxa-bicyclo[3.1.0]hexan-2-one 

Relevant academic research and scientific papers

Stereoselective synthesis of enantiopure cyclopropane didehydroamino acid derivatives: (-)-(Z)-2-benzyloxycarbonylamino-4,5-cyclopropane-2-hexenodioic acid dimethyl ester

The title amino acid derivative has been synthesized stereoselectively in 40% overall yield from 5-tert-butyldiphenylsilyloxymethyl-2(5H)-furanone used as a chiral precursor.

Controlling π-Facial Diastereoselectivity in the 1,3-Dipolar Cycloadditions of Diazomethane to Chiral Pentenoates and Furanones: Enantioselective Stereodivergent Syntheses of Cyclopropane Hydroxy Acids and Didehydro Amino Acids

The title compounds have been synthesized in both enantiomeric forms and in good overall yields by using D-glyceraldehyde as the single chiral precursor. The efficiency and usefulness of the synthetic routes have been secured by performing controlled manipulations of the functional groups and by highly stereoselective transformations, namely Wittig-Horner condensations and cyclopropanations. Cyclopropane derivatives have been synthesized through 1,3-dipolar cycloaddition of diazomethane to chiral pentenoates or furanones obtained, in turn, from D-glyceraldehyde. Syn/ anti stereochemistry of the cycloadducts has been unequivocally assigned and rationalized. Since π-facial diastereoselectivity involved in these cycloadditions is the opposite for cyclic and open- chain structures, enantiomeric series of products can be derived.

STEREOCHEMICAL CONTROL OF NATURE'S BIOSYNTHETIC PATHWAYS: A GENERAL STRATEGY FOR THE SYNTHESIS OF POLYPROPIONATE-DERIVED STRUCTURAL UNITS FROM A SINGLE CHIRAL PROGENITOR

A general strategy that permits the stereocontrolled construction of acyclic chains containing vicinal and/or alternating alkyl and hydroxy substituents is presented.Structural subunits of ionomycin were synthesized from a common chiral intermediate.

A Versatile Protocol for the Stereocontrolled Elaboration of Vicinal Secondary and Tertiary Centers of Relevance to Natural Product Synthesis

Chiral butenolides derived from L-glutamic acid, D-ribonolactone, or D-mannitol are versatile templates from the stereocontrolled introduction of functional groups.Vicinal and/or alternating patterns of secondary and tertiary substitution can be attained