667429-83-6

Upstream product

• 1241411-26-6 (2R,3S)-1-amino-pent-4-ene-2,3-diol hydrochloride 
• 1101174-59-7 (2S,3S)-1-amino-pent-4-ene-2,3-diol hydrochloride 
• 144-55-8 sodium hydrogencarbonate 
• 1101174-61-1 (2S,3R)-1-amino-pent-4-ene-2,3-diol hydrochloride 
• 1221418-82-1 (2R,3R)-1-aminopent-4-ene-2,3-diol hydrochloride 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 81026-76-8 ((3aR,4R,6aR)-6-methoxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl methanesulfonate 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 532-20-7 D-Ribose 
• 152785-75-6 (3aS,4S,6aR)-tert-butyl 4-(hydroxymethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate 
• 177569-80-1 ((3aR,4S,6aS)-5-benzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl)methanol 
• 532-20-7 D-lyxose 
• 205444-34-4 (S)-tert-butyl 2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 571201-15-5 (S)-5,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-3-one 

Downstream Products

• 127910-61-6 (1R,5S,6S)-tert-butyl 6-formyl-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane-7-carboxylate 
• 98632-49-6 3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine 

Relevant academic research and scientific papers

A novel and environmental friendly synthetic route for hydroxypyrrolidines using zeolites

A critical step in the synthesis of the hydroxypyrrolidines, 1,4-dideoxy-1,4-imino-L-lyxitol and 1,4-dideoxy-1,4-imino-D-lyxitol, from the corresponding D-sugars is the synthesis of O-methyl 2,3-O-isopropylidenepentofuranoses. Instead of applying homogeneous catalysis process with conventional inorganic acid catalysts like HCl and HClO4, it was found that heterogeneous catalysis using zeolites could be used for the one-pot synthesis of O-methyl 2,3-O-isopropylidenepentofuranoses directly from D-sugars, MeOH and acetone at mild condition. The best catalyst was H-beta zeolite containing a Si/Al molar ratio of 150, where a yield of >83% was obtained. The overall yields of the five-step procedure to 1,4-dideoxy-1,4-imino-L-lyxitol and 1,4-dideoxy-1,4-imino-D-lyxitol were 57% and 50%, respectively. This synthetic procedure has several advantages such as competitive overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the zeolite catalyst can be easily recovered from the reaction mixture and reused with no loss of activity.

Pyrrolidine-Based P,O Ligands from Carbohydrates: Easily Accessible and Modular Ligands for the Ir-Catalyzed Asymmetric Hydrogenation of Minimally Functionalized Olefins

The potential of P,O-iminosugar based ligands in the Ir-catalyzed asymmetric hydrogenation of minimally functionalized olefins is presented. These new ligands were prepared from easily available carbohydrates (D-mannose, D-ribose and D-arabinose). The stereochemical and polyfunctional diversity of carbohydrates allowed the modulation of the ligands, both from their electronic properties and the rigidity of their backbone. High enantioselectivities (ee’s up to 99 %) can be reached in the hydrogenation of selected tri- and disubstituted substrates.

Synthesis and anti-tuberculosis activity of glycitylamines

A series of glycitylamines, which were prepared in few steps from readily available carbohydrates, were tested for their ability to inhibit tuberculosis growth in an Alamar Blue BCG colourimetric assay. Several derivatives, including (2R,3R)-1-(hexadecyla

A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines

A five-step, protecting group free synthesis of 2,3-cis substituted hydroxy-pyrrolidines is presented. Key steps in the synthesis are the chemoselective formation of a primary amine via a Vasella reductive amination using ammonia as the nitrogen source, and the stereoselective formation of a cyclic carbamate from an alkenylamine. Improvement of the reductive amination, by way of the use of α-picoline borane as a more environmentally benign reducing agent, is also presented.

METHODS FOR THE PREPARATION OF ALKENYLAMINES, CYCLIC CARBAMATES OR DITHIOCARBAMATES, AND AMINOALCOHOLS OR AMINOTHIOLS

A method for preparing an alkenylamine, or a salt, solvate or hydrate thereof, is disclosed. The method comprises reacting a alogen-substituted cyclic acetal or a derivative thereof under particular conditions to provide the alkenylamine, which may be optionally converted into a salt, solvate or hydrate thereof. A method for preparing a cyclic carbamate or cyclic dithiocarbamate, or a salt, solvate or hydrate thereof, is also disclosed. The method comprises reacting an alkenylamine under particular conditions to provide the cyclic carbamate or cyclic dithiocarbamate, which may be optionally converted into a salt, solvate or hydrate thereof. A method for preparing a 1,2-aminoalcohol or 1,2-aminothiol, or a salt, solvate or hydrate thereof, is also disclosed. The method comprises forming a cyclic carbamate or cyclic dithiocarbamate from an alkenylamine, and deprotecting the cyclic carbamate or cyclic dithiocarbamate to provide the 1,2-aminoalcohol or 1,2-aminothiol, which may optionally be converted into a salt, solvate or hydrate thereof.

Total synthesis without protecting groups: Pyrrolidines and cyclic carbamates

(Chemical Equation Presented) A protecting group free synthesis of 2,3-cis substituted hydroxypyrrolidines is reported. Two novel reaction methodologies allow for the stereoselective formation of cyclic carbamates from olefinic amines, and the formation o

The combined use of stereoelectronic control and ring closing metathesis for the synthesis of (-)-8-epi-swainsonine

A novel and efficient synthesis of (-)-8-epi-swainsonine 2 is reported. Stereocontrolled diol formation from the bicyclic alkene 3 followed by a stereoselective vinylation of the aldehyde and ring closing metathesis gave the indolizidine ring system, which was converted into (-)-8-epi-swainsonine 2.

A convenient approach to (-)-8-epi-swainsonine

A novel and efficient synthesis of (-)-8-epi-swainsonine (2) is reported. Face-selective diol formation from the bicyclic alkene 3 followed by a stereoselective vinylation of the aldehyde and ring-closing metathesis gave the indolizidine ring system, which was converted into (-)-8-epi-swainsonine (2). Georg Thieme Verlag Stuttgart.

Novel routes to the kainates: Stereoselectivity in addition reactions to pyrrole [1,2c]-oxazol-3-one

This paper describes the addition of a range of electrophiles to 1. An unusual and unpredicted stereochemistry of addition has been observed in line with our original photochemical observations.

A New Strategy for the Diastereoselective Synthesis of Polyfunctionalized Pyrrolidines

This paper describes a new strategy for the synthesis of polyfuncticnalized pyrrolidines via the ring-closing metathesis reaction of substituted 3-allyl-4-vinyl-2-oxazolindones and subsequent diastereoselective cis-dihydroxylation of the resulting pyrrolo