109124-35-8

Upstream product

• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 19728-63-3 N-benzyloxycarbonyl-L-treonine 
• 501-53-1 benzyl chloroformate 
• 104410-78-8 (2S,3R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate 

Downstream Products

• 109215-72-7 >-<1-<1-<<(1,1-(dimethylethyl)dimethyl)silyl>oxy>ethyl>-4-oxo-2-pentenyl>carbamic acid phenylmethyl ester 
• 104427-25-0 <4R-<4α,5β,6α(1R*,2R*)>>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<<(phenylmethoxy)carbonyl>amino>propyl>-5-hydroxy-1-cyclohexene-1-carboxylic acid methyl ester 
• 109124-44-9 ((3R,4R,4aR,5R,6R,8R,8aS)-5,6,8-Trihydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl)-carbamic acid benzyl ester 
• 109124-38-1 ((3R,4R,4aS,5S,6S,8S,8aS)-5,6,8-Trihydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl)-carbamic acid benzyl ester 
• 104410-88-0 <3aS-(3aα,5α,6β,6aβ,7β,8β,10aS*)>-<5,6-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydro-8-methyl-10-oxo-2-thioxo-5H,10H-1,3-dioxolo<4,5-i><2>benzopyran-7-yl>carbamic acid phenylmethyl ester 
• 109124-36-9 [(3R,4R,4aS,5S,6S,8S,8aR)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8,8a-dihydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl]-carbamic acid benzyl ester 
• 109124-37-0 [(3R,4R,4aS,5S,6S,8S,8aS)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-3-methyl-1-oxo-octahydro-isochromen-4-yl]-carbamic acid benzyl ester 
• 109124-46-1 <3'aR-(3'aα,8'β,9'β,9'aα,9'bβ)>-(3'a,4',8',9',9'a,9'b-hexahydro-5'-hydroxy-8'-methyl-6'-oxospirodioxolo<4,5f><2>benzopyran>-9'-yl)carbamic acid phenylmethyl ester 
• 109124-45-0 C₂₄H₃₁NO₇ 
• 109124-39-2 ((3aS,5S,5aS,8R,9R,9aS,9bS)-5-Hydroxy-2,2,8-trimethyl-6-oxo-octahydro-[1,3]dioxolo[4,5-f]isochromen-9-yl)-carbamic acid benzyl ester 
• 109124-43-8 <1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester 
• 104486-65-9 (4S,5S,6S)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 104410-81-3 (S)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester 
• 104486-64-8 (R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Stereoselective allylation reactions of acyclic and chiral α-amino-β-hydroxy aldehydes

Stereoselective allylation reactions of acyclic and chiral α-amino-β-hydroxy aldehydes affording chiral β-amino-α,γ-diols are described. Several Lewis acids (BF3·OEt2, SnCl4, TiCl4, ZnCl2, and MgBr2·OEt2) were employed to mediate the allylation reactions. The reactions of anti-α-NHCbz-β-OTBS substrates mediated by SnCl4 afforded syn-selective products. The same reaction conditions also gave satisfactory results for the reactions of syn-α-NHCbz-β-OTBS substrates. The mechanism involves α-chelation between the amido group and aldehyde oxygen.

Stereoselective allylation of acyclic and chiral α-amino-β-Hydroxy aldehydes part 2: Application to the formal synthesis of the polyhydroxylated γ-amino acid (+)-Detoxinine

Stereoselective allylations of acyclic, chiral α-amino-β-hydroxy aldehydes mediated by BF3·OEt2 and its application to the formal synthesis of the polyhydroxylated γ-amino acid (+)-detoxinine are described. The reactions of syn-α-NHC

π-Facial selection in intermolecular Diels-Alder reactions: Total syntheses of (+)-actinobolin and (+)-5,6,10-triepi-actinobolin

Syntheses of both 5,6,10-triepi-actinobolin and the antibiotic actinobolin are described in which a homochiral diene prepared from L-threonine is employed as a key componenet in a Diels-Alder reaction with an acetylenic dienophile. While the Diels-Alder reaction of this diene with methyl propiolate furnished the cycloadduct required for the synthesis of (+)-actinobolin as the minor diastereomer, the completion of the synthesis required but seven additional steps. The steric and stercoelectronic features responsible for the π-facial course of this cycloaddition reaction are discussed along with the various steps required to complete the syntheses of the title compounds.