181303-65-1

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 131319-74-9 (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine 
• 3536-96-7 vinylmagnesium chloride 
• 100777-91-1 (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 
• 181303-70-8 N-Benzyl-N-[(S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-trimethylsilanyl-prop-2-ynyl]-hydroxylamine 
• 198418-07-4 N-Benzyl-N-[(S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-prop-2-ynyl]-hydroxylamine 
• 91190-38-4 N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 
• 100-46-9 benzylamine 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 181303-61-7 (3S,4S)-3-(N-benzylhydroxylamino)-4,5-dihydroxy-4,5-O-isopropylidene-1-pentene 

Downstream Products

• 194422-04-3 (3S,4S)-N-benzyl-N-(tert-butoxycarbonyl)-4,5-O-isopropylidene-4,5-dihydroxypent-1-en-3-amine 
• 668994-33-0 Allyl-benzyl-[(S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyl]-amine 
• 668994-39-6 N-benzyl-N-[1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-allyl]-acrylamide 
• 600728-80-1 Benzyl-[(S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-propyl]-carbamic acid tert-butyl ester 
• 1134205-62-1 C₁₉H₂₅NO₃ 
• 1029537-96-9 N-Benzyl-N-[(1S)-1-(hydroxymethyl)propyl]-4-methylbenzenesulfonamide 
• 1300117-03-6 N-benzyl-N-[(1S)-((1S)-1,2-dihydroxy)ethylprop-2-enyl]-4-methylbenzenesulfonamide 
• 668994-40-9 (3R,4R,5S)-1-Benzyl-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-pyrrolidin-2-one 
• 858656-63-0 (2S,3R,4S)-1-Benzyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pyrrolidine-3,4-diol 
• 668994-37-4 (2S,3S,4R)-1-Benzyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pyrrolidine-3,4-diol 
• 668994-35-2 (S)-1-benzyl-2,5-dihydro-2-((S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1H-pyrrole 
• 210415-92-2 (S)-1-Benzyl-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1,5-dihydro-pyrrol-2-one 
• 137146-84-0 (2S,3S)-3-benzylamino-4-pentene-1,2-diol 

Relevant academic research and scientific papers

A convenient synthesis of L-α-vinylglycine from D-mannitol

A novel procedure is described for the synthesis of L-α-vinylglycine based on the diastereoselective addition of vinylmagnesium bromide to the N- benzyl imine derived from 2,3-O-isopropylidene-D-glyceraldehyde. The route developed is both convenient (only

Synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, l-allitol and d-talitol: a stereo selective approach for azasugars

A stereo selective approach for the azasugars 1,4-dideoxy-1,4-imino-d-allitol, l-allitol, and 1,4-dideoxy-1,4-imino-d-talitol is described for different olefin compounds I derived from (R)-2,3-O-isopropylidine glyceraldehyde, l-ascorbic acid, and d-isoascorbic acid by using vinyl Grignard addition, allylation, RCM, and dihydroxylation as the key steps.

Stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline

A stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol 1 and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline was achieved via the addition of vinylmagnesium bromide to the benzylimine derived from (R)-2,3-O-isopropylidene glyceraldehyde followed by N-allylation, ring-closing metathesis (RCM), and dihydroxylation.

Study of the reactions between vinylmagnesium bromide and imines derived from (R)-glyceraldehyde - The key step in the stereodivergent synthesis of conveniently protected, enantiopure syn- and anti-2-amino-1,3,4-butanetriol derivatives

A total stereodivergent method for the synthesis of enantiopure syn- and anti-2-amino-1,3,4-butanetriol (ABT) derivatives from inexpensive and readily available D-mannitol has been developed. Key steps include: (a) the diastereoselective addition of vinylmagnesium bromide to conveniently protected N-benzylimines derived from (R)-glyceraldehyde, and (b) the oxidative degradation of the C-C double bond of the resultant syn- and anti-vinylaminodiol derivatives. The addition of vinylmagnesium bromide in diethyl ether to the N-benzylimine derived from (R)-2,3-O-isopropylideneglyceraldehyde affords the anti-vinylaminodiol derivative, while the reaction with the N-benzylimine derived from (R)-2,3-di-Obenzylglyceraldehyde affords the syn-vinylaminodiol derivative, both with excellent diastereoselectivities (de > 98/2). Moreover, a reversal of the stereochemical course of the reaction is produced when (R)-2,3-O-isopropylideneglyceraldehyde N-benzylimine is precomplexed with ZnI2, in this case yielding the syn addition adduct as the major compound. Different reaction conditions (reagent molar ratio, reaction temperature) have been tested in order to determine their influences on the observed yields and diastereo-selectivities. From the results of this study and a subsequent crossover experiment, some interesting mechanistic considerations can be inferred. Enantiopure anti- and syn-vinylaminodiol adducts have been successfully converted into conveniently protected anti- and syn-2-amino-1,3,4-butanetriol (ABT) derivatives, key building blocks in the asymmetric synthesis of biologically active compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

A short and efficient synthesis of (-)-4a,5-dihydrostreptazolin

(-)-4a,5-Dihydrostreptazolin has been synthesized in 9 steps from D- glyceraldehyde acetonide. Key steps include a diastereoselective addition of a vinylic Grignard reagent onto an imine, a ring-closing metathesis and a highly stereoselective enyne radical-mediated cyclization.

A general method for the vinylation of nitrones. Synthesis of allyl hydroxylamines and allyl amines

An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to α-alkoxy nitrones, the same reaction with α-amino nitrones gave syn add

Direct vinylation and ethynylation of nitrones. Stereodivergent synthesis of allyl and propargyl amines

The addition of vinyl and ethynyl organometallic reagents to the nitrone derived from D-glyceraldehyde affords allyl and propargyl hydroxylamines which are easily converted into the corresponding allyl and propargyl amines. The stereoselectivity of the addition step can be controlled by the presence (or absence) of diethyl aluminium chloride.