90633-95-7

Upstream product

• 94902-60-0 methyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 
• 495378-99-9 methyl 2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-α-D-glucopyranoside 
• 111727-15-2 (2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-ol 
• 824-94-2 p-methoxybenzyl chloride 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 20231-38-3 (2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)tetrahydro-6-methoxy-2-((trityloxy)methyl)-2H-pyran-3-ol 
• 123-11-5 4-methoxy-benzaldehyde 
• 162680-20-8 methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside 
• 105-13-5 4-Methoxybenzyl alcohol 
• 1450734-54-9 4-methoxybenzyl N-phenyl-2,2,2-trifluoroacetimidate 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 161443-22-7 methyl 4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 

Downstream Products

• 130523-98-7 (2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 495379-01-6 methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-6-O-triflyl-α-D-glucopyranoside 
• 273926-04-8 (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-ethynyl-6-methoxy-tetrahydro-pyran-3-ol 
• 273926-19-5 (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-prop-2-ynyl-tetrahydro-pyran-3-ol 
• 273926-13-9 (2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-2-prop-2-ynyl-octahydro-pyrano[3,2-b]pyran-3-ol 
• 273926-05-9 (E)-3-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-ethynyl-6-methoxy-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester 
• 273926-03-7 (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-ethynyl-2-methoxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran 
• 273926-16-2 (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-methoxy-5-(4-methoxy-benzyloxy)-6-prop-2-ynyl-tetrahydro-pyran 
• 273926-22-0 (E)-3-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-acrylic acid ethyl ester 
• 273926-10-6 ((2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-hydroxy-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetic acid ethyl ester 
• 273926-25-3 ((2R,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-3-methylene-octahydro-pyrano[3,2-b]pyran-2-yl)-acetic acid ethyl ester 
• 273926-12-8 ((2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-2-prop-2-ynyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-tert-butyl-dimethyl-silane 
• 273926-14-0 (E)-3-((2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-6-methoxy-2-prop-2-ynyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-acrylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of asymmetrically substituted scyllo-inositol

scyllo-Inositol, a rare member of the inositol family, is present in axinelloside A, a marine metabolite with interesting inhibitory activity against human telomerase. Here, we present a concise synthesis of asymmetrically substituted scyllo-inositol star

3-Butenyloxycarbonyl as a new hydroxyl protecting group in carbohydrate synthesis

3-Butenyloxycarbonyl (Bloc) has been identified as a new hydroxyl protecting group, which can be introduced under mild conditions in high yields and selectively removed by OsO4/NaIO4/2,6-lutidine in CH3CN-H2O wi

P-Methoxybenzyl-N-phenyl-2,2,2-trifluoroacetimidate: A versatile reagent for mild acid catalyzed etherification

PMB-NPTFA 1a is a new month bench stable and powerful reagent for the formation of PMB ethers. Several alcohols were protected in high yields and short reaction times, using low reagent loading and small catalytic amounts of Bi(OTf)3. The mild

Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation

In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra

Regio- and chemoselective reductive cleavage of 4,6-O-benzylidene-type acetals of hexopyranosides using BH3·THF-TMSOTf

Benzylidene-type cyclic acetals of carbohydrates undergo efficient reductive ring opening using BH3·THF and a catalytic amount of TMSOTf at room temperature. 4,6-O-Benzylidene-hexopyranosides afford the corresponding 4-O-benzyl ethers exclusive

Temperature-controlled regioselectivity in the reductive cleavage of p-methoxybenzylidene acetals

The regioselective ring opening of pyranosidic 4,6-p-methoxybenzylidene acetals with BH3/Bu2BOTf in THF can be tuned by adjusting the reaction temperature and reagent concentrations. Reductive cleavage at 0 °C resulted in the exclusive formation of 4-O-p-methoxybenzyl (PMB) ethers, whereas reaction at -78 °C produced 6-O-PMB ethers in high yields. The latter condition was observed to be compatible with a variety of acid-sensitive functional groups, including allyl and enol ethers. The presence of water does not interfere with reductive ring opening and may contribute toward in situ generation of H+ as a catalyst for 6-O-PMB ether formation. Reductive cleavage under rigorously aprotic conditions is greatly decelerated, and yields only the 4-O-PMB ether. The temperature-dependent reductive cleavage of the 4,6-acetal can be described in terms of kinetic versus thermodynamic control: Lewis-acid coordination of the more accessible O-6 is favored at higher temperatures, whereas protonation of the more basic but sterically encumbered O-4 predominates at low temperatures.

Stereocontrolled formation of oxacephams from carbohydrates

The [2+2] cycloaddition of chlorosulfonyl isocyanate to (Z)-4-O-propenyl ethers 16, 17, 29 and 30 proceeds with an excellent stereoselectivity in the case of ether 16 and with moderate stereoselectivity in remaining cases. Adducts were transformed into corresponding oxacephams: 37 in the first case, a mixture of 37/40 in the second and third case, and a mixture of 50/51 in the last case. In all instances addition to the si-re side of the olefin dominates. Oxacephams 41 and 52 with opposite R-configuration at the bridgehead carbon C-5a can be obtained by the alternate methodology based on the alkylation of nitrogen in 4-vinyloxyazetidin-2-one by protected 6-O-triflate 24 or 25, followed by cyclization via intramolecular displacement of the vinyloxy group. Compounds 37, 40, 41, 50, 51 and 52 constitute a convenient entry leading to polyfunctionalized oxacephams.

Synthesis of L-α-phosphatidyl-D-myo-inositoi 5-phosphate and L-α- phosphatidyl-D-myo-inositol 3,5-bisphosphate

Two new 5-phosphorylated phosphatidylinositols have been synthesized from methyl α-D-glucopyranoside as the chiral precursor. These new PtdInsP(n)s have been recently detected in mammalian cells.

Chiral Synthesis of the BC-Ring System of Ciguatoxin from D-Glucose

The BC-ring system of ciguatoxin was stereoselectively synthesized by 12 steps from methyl α-D-glucopyranoside.

Synthesis of P-5 tethered inositol-1,2,6-trisphosphate, an affinity reagent for α-trinositol receptors

The synthesis of D-myo-P-5-(O-aminopropyl)-Ins(1,2,5,6)P4, a phosphodiester analog of Ins(1,2,6)P3 tethered at the C-5 position, has been achieved and a photoaffinity label has been prepared.