92206-12-7

Upstream product

• 100-39-0 benzyl bromide 
• 700367-73-3 (2S,3S)-3-hydroxy-2,3-bis(benzyloxy)propionaldehyde 
• 302579-03-9 (4S,5R)-5-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxane 
• 20638-61-3 (4S,5R)-4-(hydroxymethyl)-2-phenyl-1,3-dioxan-5-ol 
• 100-44-7 benzyl chloride 
• 92231-33-9 1,3-di-O-benzyl-2,4-O-ethylidene D-erythritol 
• 119770-87-5 (2R,3R)-diethyl 2-(benzyloxy)-3-hydroxysuccinate 
• 84379-51-1 2-O-benzyl-L-threitol 
• 35572-34-0 (4S,5S)-4,5-dihydroxymethyl-2-phenyldioxolane 
• 35572-31-7 (4R,5R)-2-Phenyl-1,3-dioxolan-4,5-dicarbonsaeure-diethylester 
• 774-48-1 (diethoxymethyl)benzene 
• 107938-32-9 (2S,3S)-1,2-O-Benzylidene-3-O-benzylthreitol 

Downstream Products

• 1395045-12-1 (2S,3S)-1,3-bis(benzyloxy)-4-(octanoyloxy)butan-2-yl octanoate 
• 1395045-10-9 (2S,3S)-1,3-bis(benzyloxy)-4-(hexadecanoyloxy)butan-2-yl hexadecanoate 
• 1271742-09-6 C₃₀H₅₀O₄Si₂ 
• 92206-15-0 1,3-di-O-benzyl-4-O-trityl-D-glycero-tetrulose 
• 92206-16-1 1,3-di-O-benzyl-4-O-(tert-butyldimethylsilyl)-D-glycero-tetrulose 
• 90302-18-4 1,3-di-O-benzoyl-D-glycero-tetrulose 
• 155650-43-4 1,3-diazido-2,4-di-O-benzyl-1,3-dideoxy-D-threitol 
• 155650-45-6 5(R)-benzyloxy-4(R)-benzyloxymethyl-tetrahydropyrimidin-2-one 
• 163211-53-8 1,3-Diamino-2,4-di-O-benzyl-1,3-didesoxy-D-threitol 
• 302579-04-0 2,4-di-O-benzyl-L-erythritol-1,3-O-cyclic sulfate 
• 445424-42-0 (4S,5R)-5-Benzyloxy-4-benzyloxymethyl-[1,3,2]dioxathiane 2-oxide 
• 155650-40-1 1,3-di-O-benzyl-2,4-di-O-p-tolylsulfonyl-D-erythritol 
• 92206-14-9 2,4-di-O-benzyl-1-O-(tert-butyldimethylsilyl)-L-erythritol 
• 92206-13-8 (2S,3R)-1,3-Bis-benzyloxy-4-trityloxy-butan-2-ol 

Relevant academic research and scientific papers

Tertiary Amine Promoted Asymmetric Aldol Reaction of Aldehydes

The direct asymmetric self-aldol reactions of various α-oxyaldehydes catalyzed by tertiary amines have been demonstrated. By using 10 mol-% of quinine catalyst, dimerization products have been prepared in high yields, with good anti-diastereocontrol, and up to 80% ee. The presented enolate-mediated synthesis of protected tetrose sugars has never been accomplished before by chiral tertiary amine organocatalysts.

Development of diacyltetrol lipids as activators for the C1 domain of protein kinase C

The protein kinase C (PKC) family of serine/threonine kinases is an attractive drug target for the treatment of cancer and other diseases. Diacylglycerol (DAG), phorbol esters and others act as ligands for the C1 domain of PKC isoforms. Inspection of the crystal structure of the PKCδ C1b subdomain in complex with phorbol-13-O-acetate shows that one carbonyl group and two hydroxyl groups play pivotal roles in recognition of the C1 domain. To understand the importance of two hydroxyl groups of phorbol esters in PKC binding and to develop effective PKC activators, we synthesized DAG like diacyltetrols (DATs) and studied binding affinities with C1b subdomains of PKCδ and PKC. DATs, with the stereochemistry of natural DAGs at the sn-2 position, were synthesized from (+)-diethyl l-tartrate in four to seven steps as single isomers. The calculated EC50 values for the short and long chain DATs varied in the range of 3-6 μM. Furthermore, the fluorescence anisotropy values of the proteins were increased in the presence of DATs in a similar manner to that of DAGs. Molecular docking of DATs (1b-4b) with PKCδ C1b showed that the DATs form hydrogen bonds with the polar residues and backbone of the protein, at the same binding site, as that of DAG and phorbol esters. Our findings reveal that DATs represent an attractive group of C1 domain ligands that can be used as research tools or further structurally modified for potential drug development.

The first total synthesis and structural determination of antibiotics K1115 B1s (alnumycins)

K1115 B1, isolated from the broth of Streptomyces species, was found to be a mixture of stereoisomers. Authors synthesized all stereoisomers of K1115 B1 by convergent synthesis coupling a rhamnose derivative, an isobenzofuranone, and a chiral tetraol. Comparison of 1H NMR spectra and optical rotations made it clear that the absolute structures of K1115 B 1α (the major isomer) and K1115 B1β (the minor isomer) were (1R, 17S)- and (1R, 17R)-configurations, respectively. The optical rotations of the stereoisomers revealed that alnumycin, reported as the identical structure with K1115 B1, might be another mixture of stereoisomers.

Chiral primary-tertiary diamine-bronsted acid salt catalyzed syn-selective cross-aldol reaction of aldehydes

(Figure presented) Highly syn-selective cross-aldol reaction of aldehydes has remained a challenging subject in the field of aminocatalysis. To achieve this end, chiral primary amines have been explored and the primary-tertiary diamine-Bronsted acid salts are found to promote the cross-aldol reactions of aldehydes with high activity and syn selectivity. Among various vicinal diamines screened, l-phenylalanine derived 2a/TfOH conjugate is identified as the optimal catalyst, showing good catalytic activity (up to 97% yield) and high syn selectivities (syn/anti up to 24:1, 87% ee). The current catalysis works selectively with small aliphatic aldehydes donors such as propionaldehyde and isobutyraldehyde, but not with aliphatic aldehydes bearing larger β-substitute (>Me). In addition, the use of 2a/TfOH conjugate has also enabled the first syn-selective cross-aldol reactions of glycoaldehyde donors.

Acceptor specificity in the transglycosylation reaction using Endo-M

To determine the structural specificity of the glycosyl acceptor of the transglycosylation reaction using endo-β-N-acetylglucosaminidase (ENGase) (EC 3.2.1.96) from Mucor hiemalis (Endo-M), several acceptor derivatives were designed and synthesized. The narrow regions of the 1,3-diol structure from the 4- to 6-hydroxy functions of GlcNAc were found to be essential for the transglycosylation reaction using Endo-M. Furthermore, it was determined that Endo-M strictly recognizes a 1,3-diol structure consisting of primary and secondary hydroxyl groups.

Efficient synthesis of the glucosidase inhibitor blintol, the selenium analogue of the naturally occurring glycosidase inhibitor salacinol

(Chemical Equation Presented) An efficient synthesis of blintol, the selenium congener of the naturally occurring glycosidase inhibitor salacinol, and a potent glucosidase inhibitor itself, is described. Unlike our previously reported synthesis, this impr

Amino acid catalyzed neogenesis of carbohydrates: A plausible ancient transformation

Hexose sugars play a fundamental role in vital biochemical processes and their biosynthesis is achieved through enzyme-catalyzed pathways. Herein we disclose the ability of amino acids to catalyze the asymmetric neogenesis of carbohydrates by sequential cross-aldol reactions. The amino acids mediate the asymmetric de novo synthesis of natural L- and D-hexoses and their analogues with excellent stereoselectivity in organic solvents. In some cases, the four new stereocenters are assembled with almost absolute stereocontrol. The unique feature of these results is that, when an amino acid is employed as the catalyst, a single reaction sequence can convert a protected glycol aldehyde into a hexose in one step. For example, proline and its derivatives catalyze the asymmetric neogenesis of allose with > 99% ee in one chemical manipulation. Furthermore, all amino acids tested catalyzed the asymmetric formation of natural sugars under prebiotic conditions, with alanine being the smallest catalyst. The inherent simplicity of this catalytic process suggests that a catalytic prebiotic "gluconeogenesis" may occur, in which amino acids transfer their stereochemical information to sugars. In addition, the amino acid catalyzed stereoselective sequential cross-aldol reactions were performed as a two-step procedure with different aldehydes as acceptors and nucleophiles. The employment of two different amino acids as catalysts for the iterative direct aldol reactions enabled the asymmetric synthesis of deoxysugars with > 99% ee. In addition, the direct amino acid catalyzed C2+C 2+C2 methodology is a new entry for the short, highly enantioselective de novo synthesis of carbohydrate derivatives, isotope-labeled sugars, and polyketide natural products. The one-pot asymmetric de novo syntheses of deoxy and polyketide carbohydrates involved a novel dynamic kinetic asymmetric transformation (DYKAT) mediated by an amino acid.

Synthesis of salacinol

Salacinol, a new type of α-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sul

Competitive inhibition of glycoside hydrolases by 1,3-diamino-1,3-dideoxy-tetritols and their cyclic carbonic and thiocarbonic amides

1,3-Diamino-1,3-dideoxy-D-threitol (1) and the corresponding 1,3-diamino-1,3-dideoxy-D-erythritol (2) were synthesised starting from D-glucose and L-arabinose, respectively.These acyclic diamines inhibited competitively both β-D-glucosidase from sweet almond emulsin and β-D-galactosidase from E. coli with Ki-values ranging from 3 to 10 mM.When the suitably blocked diamines were reacted with activated carbonic and thiocarbonic acid derivatives, cyclic urea 5(R)-hydroxy-4(R)-hydroxymethyl-tetrahydropyrimidin-2-one (13), 5(S)-hydroxy-4(R)-hydroxymethyl-tetrahydropyrimidin-2-one (15) and thiourea 5(S)-hydroxy-4(R)-hydroxymethyl-tetrahydropyrimidin-2-thione (18) derivatives were obtained, which conformationally resemble the envelope structure of the D-glucopyranosyl or the D-galactopyranosyl cation.The cyclic carbonamides showed extremely weak competitive inhibition but only with their corresponding enzymes.Compounds 15 and 18 exist, as indicated by 1H NMR spectroscopy, in an unexpected E-conformation with axial substituents.Upon per-O-acetylation the expected conformation with equatorial substituents is adopted.

Selective Manipulation of Hydroxy Groups in (2S,3S)-Threitol

Systematic transformation of diethyl (2R,3R)-tartrate into a number of protected or functionalized derivatives of threitol, which are important precursors for many natural products, is carried out employing reductive and oxidative cleavage reactions of be