19131-10-3

Upstream product

• 71811-64-8 Methyl 2,3-anhydro-4,6-bis-α-D-allopyranoside 
• 33650-60-1 methyl 3,4-di-O-acetyl-2,6-dideoxy-α-D-ribo-hexopyranoside 
• 107908-90-7 methyl 2,6-dideoxy-4-O-p-tolylsulfonyl-α-D-ribo-hexapyranoside 
• 109-99-9 tetrahydrofuran 
• 959412-03-4 methyl 4-O-benzoyl-6-deoxy-2-O-tosyl-α-D-mannopyranoside 
• 1345697-37-1 methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside 
• 67-56-1 methanol 
• 55533-58-9 2,3-anhydro-6-deoxy-1-O-methyl-α-D-allopyranoside 
• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 18933-59-0 2,3-anhydro-4-O-benzoyl-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside 
• 62131-22-0 2,3-anhydro-6-bromo-6-deoxy-1-O-methyl-α-D-allopyranoside 
• 2053-00-1 D-digitoxose 
• 78464-95-6 methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranoside 
• 51020-42-9 2-deoxy-α-L-fucopyranose 

Downstream Products

• 527-52-6 D-digitxose 
• 116500-85-7 methyl 3,4-O-benzylidene-2,6-dideoxy-α-D-ribo-hexopyranoside 
• 63592-82-5 Methyl 3-O-benzyl-2,6-dideoxy-α-D-ribo-hexopyranoside 
• 98292-31-0 methyl 2,6-dideoxy-3,4-bis-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside 
• 107908-90-7 methyl 2,6-dideoxy-4-O-p-tolylsulfonyl-α-D-ribo-hexapyranoside 
• 107908-91-8 methyl 2,6-dideoxy-3,4-di-O-p-tolylsulfonyl-α-D-ribo-hexapyranoside 
• 91732-82-0 ethyl 2,6-dideoxy-3,4-bis-O-(p-methoxybenzoyl)-1-thio-α-D-ribo-hexopyranoside 
• 148944-25-6 Methyl 4-azido-3-O-benzyl-2,4,6-trideoxy-α-D-xylo-hexopyranoside 
• 63592-81-4 Methyl 3-O-benzyl-2,6-dideoxy-4-O-tosyl-α-D-ribo-hexopyranoside 
• 139190-82-2 (3aR,4R,6R,7aS)-6-Cyclohexylmethoxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 139190-81-1 (3aR,4R,6S,7aS)-6-Cyclohexylmethoxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 141805-54-1 (2R,3S,4S)-2-Methyl-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol 
• 139190-72-0 (3aR,4R,7aS)-2,2,4-Trimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 135197-78-3 Acetic acid (2R,3R,4S)-3-acetoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

A Change from Kinetic to Thermodynamic Control Enables trans-Selective Stereochemical Editing of Vicinal Diols

Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under

A Unified Strategy to Access 2- And 4-Deoxygenated Sugars Enabled by Manganese-Promoted 1,2-Radical Migration

The selective manipulation of carbohydrate scaffolds is challenging due to the presence of multiple, nearly chemically indistinguishable O-H and C-H bonds. As a result, protecting-group-based synthetic strategies are typically necessary for carbohydrate modification. Here we report a concise semisynthetic strategy to access diverse 2- and 4-deoxygenated carbohydrates without relying on the exhaustive use of protecting groups to achieve site-selective reaction outcomes. Our approach leverages a Mn2+-promoted redox isomerization step, which proceeds via sugar radical intermediates accessed by neutral hydrogen atom abstraction under visible light-mediated photoredox conditions. The resulting deoxyketopyranosides feature chemically distinguishable functional groups and are readily transformed into diverse carbohydrate structures. To showcase the versatility of this method, we report expedient syntheses of the rare sugars l-ristosamine, l-olivose, l-mycarose, and l-digitoxose from commercial l-rhamnose. The findings presented here validate the potential for radical intermediates to facilitate the selective transformation of carbohydrates and showcase the step and efficiency advantages attendant to synthetic strategies that minimize a reliance upon protecting groups.

Synthesis of ribo-hexopyranoside- and altrose-based azacrown ethers and their application in an asymmetric Michael addition

The synthesis of four new ribo-hexopyranoside-based chiral lariat ethers of monoaza-15-crown-5 type and two altropyranoside-based crown ethers were elaborated. Our syntheses utilized the regioselective ring opening of the oxiran moiety of the 2,3-anhydro sugars by nucleophilic reagents to afford the key intermediates. The reaction of methyl-2,3-anhydro-4,6-O-benzylidene-α-d- mannopyranoside with ethanolamine is especially of interest to afford a 3-substituted altropyranoside. One of the ribo-hexopyranoside-based lariat ethers with a 4-methoxyphenyl substituent induced an enantioselectivity of 80% when used as catalyst in the Michael addition of diethyl acetamidomalonate to trans-β-nitrostyrene under phase transfer catalytic conditions.

Umpolung reactivity in the stereoselective synthesis of S-linked 2-deoxyglycosides

Take control! An unprecedented sulfenylation of stereochemically defined 2-deoxyglycosyl lithium species with asymmetric sugar-derived disulfide acceptors enabled the stereoselective synthesis of both α- and β-S-linked 2-deoxyoligosaccharides. Reductive lithiation of 2-deoxyglycosyl phenylsulfides at -78°C provides predominantly axial glycosyl lithium species, which upon warming isomerize to predominantly equatorial lithium species (see scheme). Copyright

Bromodimethylsulfonium bromide catalyzed synthesis of methyl 2-dexoy-4,6-o-benzylidene galactopyranoside from galactal and the rapid route to 2,3- and 2,6-dideoxygalactopyranoses

4,6-O-Benzylidenation of D-galactal with PhCH(OCH3)2 catalyzed by bromodimethylsulfonium bromide leads to methyl 2-dexoy-4,6-O- benzylidene galactopyranoside efficiently, which serves as a key intermediate to the ready preparation of

Halichoblelides B and C, potent cytotoxic macrolides from a Streptomyces species separated from a marine fish

Halichoblelide B (1) and C (2), novel macrolides with potent cytotoxicity against tumor cells in culture, have been isolated from a strain of Streptomyces hygroscopicus originally derived from the marine fish Halichoeres bleekeri, and their absolute stereostructures have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and chemical transformations. These compounds exhibited significant cytotoxicity against human cancer cell lines.

The asymmetric syntheses of methyl D-digitoxoside, L-oleandrose and L-cymarose from methyl sorbate, an achiral precursor

The addition of 4 eq of chloral to osmundalactone (4S,5R)-4 gave quantitative formation of the hemiacetal derivative (4S,5R)-8, which was treated with methane sulfonic acid to afford the intramolecular Micheal addition product (+)-(3S,4S,5R)-9 possessing a 3,4-cis-dihydroxy-d-lactone in 78% overall yield from (4S,5R)-4. The obtained (+)-(3S,4S,5R)-9 was subsequently converted to methyl D-digitoxoside (pyranoside) (12) in 13% overall yield and methyl D-digitoxoside (furanoside) (12) in 20% overall yield. The reaction of benzyl-osmundalactone (4R,5S)-3 and MeOH in the presence of Amberlyst A-26 as a basic catalyst gave 3,4-trans-δ-lactone (-)-(3S,4R,5S)-20 in 28% yield and 3,4-cis-d-lactone (-)-(3R,4R,5S)-21 in 45% yield. Dibal-H reduction of (-)-(3S,4R,5S)-20 followed by catalytic hydrogenation gave L-oleandrose (6) in 86% overall yield, while Dibal-H reduction of (-)-(3R,4R,5S)-21 followed by catalytic hydrogenation provided L-cymarose (7) in 85% overall yield.

Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates

Digitoxin, a clinically important cardiac trisaccharide, was assembled efficiently from digitoxigenin and 3,4-di-O-tert-butyldiphenylsilyl-d- digitoxosyl o-cyclopropylethynylbenzoate in 9 steps and 52% overall yield via alternate glycosylation and protecting group manipulation. The present synthesis showcases the advantage of the gold(I)-catalyzed glycosylation protocol in the synthesis of glycoconjugates containing acid-labile 2-deoxysugar linkages.

Substrate flexibility of vicenisaminyltransferase VinC involved in the biosynthesis of vicenistatin

A glycosyltransferase VinC is involved in the biosynthesis of antitumor β-glycoside antibiotic vicenistatin. It catalyzes a glycosyl transfer reaction between dTDP-α-D-vicenisamine and vicenilactam. Previous identification of its broad substrate specifici

Deoxygenative [1,2]-hydride shift rearrangements in nucleoside and sugar chemistry: Analogy with the [1,2]-electron shift in the deoxygenation of ribonucleotides by ribonucleotide reductases

(Chemical Equation Presented) A variant of the semipinacol rearrangement that was observed in our laboratory has been applied to the synthesis of several furanose and pyranose derivatives. The process consists of an "orchestrated" [1,2]-hydride shift with