115822-55-4

Upstream product

• 115843-62-4 (S)-4-((S)-Benzyloxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 139009-66-8 (S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid 
• 194861-76-2 (S)-4-((S)-[1,3]Dithian-2-yl-hydroxy-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 437609-53-5 (4S,1'S)-4-(1'-benzyloxy-2'-tert-butyldimethylsilanyloxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 437609-52-4 (4S,1'S)-4-(2'-tert-butyldimethylsilanyloxy-1'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 437609-40-0 (S)-4-(acetoxyacetyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 437609-43-3 (4S,1'S)-4-(1',2'-dihydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 437609-39-7 (S)-1-acetoxy-3-(tert-butoxycarbonylamino)-4-hydroxybutan-2-one 
• 244023-85-6 (S)-3-(tert-butoxycarbonylamino)-1,5-dioxaspiro[3.2]hexane 
• 213338-89-7 (S)-3-(tert-butoxycarbonylamino)-2-methyleneoxetane 
• 100-39-0 benzyl bromide 
• 79265-30-8 2-(trimethylsilyl)thiazole 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 194861-77-3 (S)-4-((1S,2R)-1-Benzyloxy-2-hydroxy-hexadec-3-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 124127-33-9 tert-butyl (4S)-4-[(1S,2S)-1,2-bis(benzyloxy)-3-oxopropyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 124127-34-0 2-O-Acetyl-4-amino-3-O-benzyl-4-N-(tert-butoxycarbonyl)-4-deoxy-4,5-N,O-isopropylidene-L-arabinose 
• 124127-32-8 (S)-4-((1S,2R)-2-Acetoxy-1-benzyloxy-2-thiazol-2-yl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 124127-31-7 (S)-4-((1S,2S)-1,2-Bis-benzyloxy-2-thiazol-2-yl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 124127-35-1 O,N-Isopropylidene-N-(tert-butoxycarbonyl)-O,O-dibenzyl-C₁₈-D-ribo-sphingosine 
• 118319-72-5 (S)-4-((S)-1-Benzyloxy-2-oxo-2-thiazol-2-yl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 115889-53-7 (1R)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol 
• 149180-94-9 tert-butyl (4S,1'R)-4-(1'-benzyloxy-4'-oxobutyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 115822-52-1 (1S)-3-Amino-2-O-benzyl-3-N-(tert-butoxycarbonyl)-3-deoxy-3,4-N,O-isopropylidene-1-(2-thiazolyl)-L-erythritol 
• 104470-54-4 (1S,2R)-2,3-O-isopropylidene-1-(2-thiazolyl)-1,2,3-propanetriol 

Relevant academic research and scientific papers

Stereoselective synthesis of 2-epi-jaspine B via base-catalyzed intramolecular oxy-Michael conjugate addition approach

2-epi-Jaspine B has been synthesized starting from (-)-diethyl tartrate in 12 simple steps and 26.6% overall yield. The key intermediate was obtained via stereoselective base-catalyzed intramolecular oxy-Michael conjugate addition followed by tandem hydro

Total synthesis of a natural cerebroside from euphorbiaceae

The regioselective total synthesis of the natural cerebroside (2R,15Z)-N-{(1S,2S,3R,4R,5Z)-1-[(β-D-glucopyranosyloxy)methyl]-2,3, 4-trihydroxyheptadec-5-en-l-yl)-2-hydroxytetracos-15-enamide (2), originally isolated from Euphorbiaceae, is reported in full

Synthesis of D-erythro-dihydrosphingosine and D-xylo-phytosphingosine from a serine-derived 1,5-dioxaspiro[3.2]hexane template

Matrix presented A serine-derived 1,5-dioxaspiro[3.2]hexane template is shown to be a useful precursor for both aminodiol and aminotriol sphingoid bases by its conversion to D-erythro-dihydrosphingosine and D-xylo-phytoshingosine.

Stereocontrol in the addition of nucleophiles to an optically active aldehyde derived from L-serine, leading to a short-step synthesis of (2S,3S,4R)-phytosphingosine

The diastereoselective addition of dithianide to a chiral aldehyde derived from L-serine followed by hydrolysis of the dithiane moiety and the addition of dodecylacetylide gave diastereomerically pure aminotriol derivative which, upon hydrogenation and deprotection, afforded (2S,3S,4R)-phytosphingosine in good overall yield in enantiomerically pure form.

Stereochemistry Associated with the Addition of 2-(Trimethylsilyl)thiazole to Differentially Protected α-Amino Aldehydes. Applications toward the Synthesis of Amino Sugars ans Sphingosines

The stereochemistry and synthetic utility of the addition of 2-(trimethylsilyl)thiazole (2-TST, 1) to various N-protected α-amino aldehydes is described.The reactions of 1 with N-Boc-L-serinal acetonide (2) and N-Boc-L-threoninal acetonide (3) are essential anti diastereoselective (ds = 85-90percent) in agreement with the Felkin-Anh model for asymmetric induction, whereas the reactions with O-benzyl-NH-Boc-L-serinal (4) and NH-Boc-L-phenylalaninal (5) are syn diastereoselective (ds = 80percent).The reversal of diastereoselectivity is interpreted on the basis of a proton-bridged cyclic Cram model for asymmetric induction.Te anti-adduct derived the N-Boc-L-serinal acetonide (2) was subjected to thiazol-to-formyl unmasking to give a one-carbon higher homologue (i. e., the O,N-protected β-amino-α-hydroxy aldehyde 6a).This material serves as a precursor to ribo- and arabino-4-amino-4-deoxypentoses via a further one-carbon-chain elongation with 2-TST and to a C20 sphingosine via Wittig olefination.The above ribo-amino sugar was transformed via sequential Wittig olefination and reduction into a C18 phytosphingosine.