20672-67-7

Upstream product

• 67-56-1 methanol 
• 20672-69-9 methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 100-44-7 benzyl chloride 
• 57783-73-0 methyl 3,4-di-O-benzyl-α-D-mannopyranoside 
• 97275-50-8 (E)-(2R,3R,4R)-6-methoxy-1,3,4-tribenzyloxy-5-hexen-2-ol 
• 73045-57-5 methyl 4,6-di-O-benzyl-α-D-mannopyranoside 
• 620-05-3 iodomethylbenzene 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 178931-69-6 Acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-((2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 146864-77-9 3,4,6-tri-O-benzyl-1,2-O-(exo-methoxyethylidene)-β-D-mannopyranose 
• 1011723-04-8 glucal epoxide 
• 1067-52-3 tributyltin methoxide 

Downstream Products

• 80596-06-1 methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 80596-05-0 methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 87424-13-3 Acetic acid (2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 87424-14-4 Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 89912-37-8 Methyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(3,6-di-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosid 
• 131221-98-2 methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-O-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 81645-00-3 3,4,6-tri-O-benzyl-2-O-(3,4-di-O-benzyl-2-O-methylsulfonyl-β-L-rhamnopyranosyl)-α-D-mannopyranoside 
• 81656-55-5 3,4,6-tri-O-benzyl-2-O-(3,4-di-O-benzyl-2-O-methylsulfonyl-α-L-rhamnopyranosyl)-α-D-mannopyranoside 
• 138566-33-3 C₆₂H₆₂O₁₃ 
• 77770-57-1 methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-glucopyranoside 
• 73407-50-8 methyl 3,4,6-tri-O-benzyl-2-deoxy-2-iodo-α-D-glucopyranoside 
• 104639-38-5 3,4,6-tri-O-benzyl-2-O-methyl-β-D-glucopyranosyl fluoride 
• 104639-37-4 3,4,6-tri-O-benzyl-2-O-methyl-α-D-glucopyranosyl fluoride 
• 76251-54-2 methyl 3,4,6-tri-O-benzyl-2-O-(methylsulfonyl)-α-D-mannopyranoside 

Relevant academic research and scientific papers

A facile synthesis of neosaccharides: 2,6′-and 3,6′-ether- linked sugars

A novel synthesis of the 2,6′-O-linkage of methyl α-D-glucoside and methyl α-D-mannoside was developed based on an acetalization- reduction approach. Utilizing this approach, the 3,6′-O-linkage of methyl α-D-glucosides was also obtained. It is noteworthy

Radical Substitution of 2-Deoxy-2-lodo Pyranosides using 2,2,6,6-Tetramethylpiperidinoxy (TEMPO) Free Radical

Methyl 2-hydroxy-α-D-pyranosides were formed via photolytic radical substitution of methyl 2-deoxy-2-iodo-α-D-pyranosides with 2,2,6,6-tetramethylpiperidinoxy (TEMPO) free radical followed by zinc reduction.

Arylboronic acid-mediated glycosylation of 1,2-dihydroxyglucoses

- We explored direct dehydrative coupling of tetrahydro-2H-pyran-2,3-diol or a 1,2-dihydroxy sugar with various alcohols using a range of arylboronic acids. Among the catalysts, 2-borono-4-trifluoromethylbenzoic acid efficiently promoted acetalization of tetrahydro-2H-pyran-2,3-diol. Ferroceniumboronic acid showed the best catalytic activity for glycosylation of the 1,2-dihydroxy sugar. The major products were 1,2-cJi-a-D-glucopyranosides.

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside

We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.

A concise synthesis of single components of partially sulfated oligomannans

A concise synthesis of single components of C2 sulfated oligomannans including trimers, tetramers, and pentamers is reported. The synthesis features the application of the DMF-modulation method for the participatory thiomannoside donors in 1,2-trans α-glycosidic bond formation. The obtained oligomannans were fully characterized using 1H, 13C, COSY, and HSQC NMR spectroscopy.

Epoxidation of glycals with oxone-acetone-tetrabutylammonium hydrogen sulfate: A convenient access to simple β-D-glycosides and to α-D-mannosamine and D-talosamine donors

The addition of a phase transfer catalyst during the epoxidation of perbenzylated glycals with oxone- acetone under biphasic conditions allows their complete epoxidation. The epoxides were readily transformed into methyl 1,2-trans-β-D-glycosides or 1,2-trans-β-D-glycopyranosyl azides (D-gluco and-D-galacto configurations) bearing a free hydroxyl group at the 2-position. These glycosyl azides were converted to alkyl 1,2-trans-2-acetamido- 2-deoxy-α-D-pyranosides or alkyl 2-allyloxycarbonylamino-2- deoxy-α-D-pyranosides (D-manno and D-talo configurations) by a Staudinger reaction and a double inversion of configuration at C-1 and C-2.

Tandem epoxidation-alcoholysis or epoxidation-hydrolysis of glycals catalyzed by titanium(IV) isopropoxide or Venturello's phosphotungstate complex

Venturello's phosphotungstate complex and titanium(IV) isopropoxide [Ti(O-i-Pr)4] were successfully used as catalysts for the epoxidation-alcoholysis of glycals using hydrogen peroxide [H2O 2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O-i-Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields and high selectivities. The Venturello complex proved to be a very versatile and efficient catalyst. Apart from epoxidation-alcoholysis in alcoholic solvents it also showed activity in biphasic conditions to allow for glycosylation of long-chain alcohols and was very effective in the stereoselective dihydroxylation of benzylated glucal.

Synthesis of the repeating trisaccharide unit of the cell wall lipopolysaccharide of Escherichia coli type 8

NIS/TfOH mediated glycosidation of methyl 3,4,6-tri-O-benzyl-α-d-mannopyranoside with phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-d-mannopyranoside furnished the corresponding disaccharide derivative in excellent yield and α-selectivity. Ze?mplen deacet

Facile oxidative cleavage of 4-O-benzyl ethers with dichlorodicyanoquinone in rhamno- and mannopyranosides

On exposure to dichlorodicyanoquinone in wet dichloromethane at room temperature, equatorial 4-O-benzyl ethers are removed with moderate selectivity in the presence of other benzyl ethers in glycopyranosides and glycothiopyranosides.

Methyltrioxorhenium-catalyzed epoxidation-methanolysis of glycals under homogeneous and heterogeneous conditions

The efficient and high yielding domino epoxidation-methanolysis of glycals 8-15 has been achieved by oxidation with UHP in MeOH catalyzed by MTO. The products have been conveniently isolated as 2-acetoxy derivatives 16-23a, b by direct acetylation of the crude mixtures. Homogeneous MTO-amine complexes 5-7, heterogeneous poly(4-vinyl-pyridine)/MTO compounds I-III, and microencapsulated polystyrene/MTO systems IV-VII were also tested and demonstrated their effectiveness as catalysts for the oxidation step. The facial diastereoselectivity of the oxidation ranged from satisfactory to excellent depending on the substrate and could be optimized by ample screening of catalysts. Complete conversions of substrates and nearly quantitative yields of products were obtained under environmentally friendly experimental conditions and with the use of simple work-up procedures.