145149-85-5

Upstream product

• 2873-29-2 D-glucal triacetate 
• 13145-22-7 methyl 2-deoxy-α-D-glucopyranoside 
• 1184705-48-3 methyl 3,4-di-O-benzyl-2-deoxy-6-O-trityl-α-D-glucopyranoside 
• 1184705-42-7 methyl 3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside 
• 1184705-45-0 methyl 3,4-di-O-benzyl-2-O-(methylsulfanylthiocarbonyl)-6-O-trityl-α-D-glucopyranoside 
• 214068-17-4 methyl 2-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 57783-73-0 methyl 3,4-di-O-benzyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 67-56-1 methanol 
• 58871-10-6 3,4-di-O-benzyl-D-glucal 
• 145149-82-2 Methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(phenoxythiocarbonyl)-α-D-glucopyranoside 

Downstream Products

• 506423-02-5 C₂₁H₂₅IO₄ 
• 175844-98-1 methyl 3,4-di-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside 
• 1184705-53-0 (3R,4R,6R)-6-(benzylamino)-3,4-bis(benzyloxy)nona-1,8-diene 
• 1184705-68-7 (3R,4R,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene 
• 1184705-74-5 (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptanone 
• 1184705-70-1 (2S,3R,5R)-5-[(benzyl)(benzyloxycarbonyl)amino]-2,3-bis(benzyloxy)cycloheptanone 
• 1184705-79-0 (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene 
• 1184705-82-5 (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene 
• 1184705-76-7 (3R,4R,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)nona-1,8-diene 
• 494212-06-5 methyl (5R)-3,4-di-O-benzyl-2-deoxy-5-[3-(phenylthio)but-3-enyl]-α-D-threo-pentopyranoside 
• 494212-05-4 methyl 3,4-di-O-benzyl-2,6,7-trideoxy-α-D-arabino-hept-6-enopyranoside 

Relevant academic research and scientific papers

Mannose-binding geometry of pradimicin A

Pradimicins (PRMs) and benanomicins are the only family of non-peptidic natural products with lectin-like properties, that is, they recognize D-mannopyranoside (Man) in the presence of Ca2+ ions. Coupled with their unique Man binding ability, t

Synthesis of calystegine A3 from glucose by the use of ring-closing metathesis

A synthesis of the nortropane alkaloid calystegine A3 is described from D-glucose. The key step employs a zinc-mediated tandem reaction where a benzyl-protected methyl 6iodo glucoside is fragmented to give an unsaturated aldehyde, which is then transformed into the corresponding benzylimine and allylated in the same pot. The functionalized nona-l,8-diene, thus obtained, is converted into the sevenmembered carbon skeleton in calystegine A3 by ring-closing olefin metathesis. Subsequent deoxygenation by the BartonMcCombie protocol, hydroboration and oxidative workup followed by hydrogenolysis affords calystegine A3. The synthesis uses a total of 13 steps from glucose and confirms the absolute configuration of the natural product.

Synthesis of a-ring synthon of 19-nor-1alpha,25-dihydroxyvitamin D3 from (D)-glucose

The present invention provides a method for the synthesis of an A-ring synthon phosphine oxide used in the preparation of 19-nor vitamin D compounds, and to novel synthetic intermediates formed during the synthesis. The new method prepares the phosphine oxide from (D)-glucose.

Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides

The effect of substituents on the reactivity and stereoselectivity of the SmI2/Pd(0)-promoted ring-contraction of 5-alkynylpyranosides has been examined using substrates substituted only at selected positions. While formation of 2-ethynylcyclopentanols takes place efficiently, an internal alkyne did not afford the expected product. The presence of peripheral alkoxy substituents leads to variable stereoselectivities that depend on the number and orientation of such groups. Thus, an isolated OBn substituent at C(3) (carbohydrate numbering) exerts a significant stereochemical control while additional substitution with the same group at C(4) either enhances or drastically reduces stereoselectivity depending on its orientation (α or β, respectively).

Acetal-vinyl sulfide cyclization on sugar substrates: Effect of structure and substituent

A range of 2-deoxyfuranoside and -pyranoside derivatives were fashioned into derivatives that carry a vinyl or propenyl side chain. Extension of the alkene by a Suzuki cross-coupling reaction with 1-bromo-1-(phenylthio)ethene gave thioenol ethers as the cyclization substrates. The treatment of these substrates with BF3·Et2O in tert-butylmethyl ether below 0 °C induced cyclization to optically active bicyclic ethers. If the cyclizations are carried out in toluene as the solvent, the isomerization of the terminal thioenol ether to the inner thioenol ether can take place prior to the cyclization. The cyclization reactions can be impeded by steric and electronic factors. The opening of the bicyclic ethers could be illustrated with the base-induced conversion of the ketone 53 to the cyclooctenone 54.

Novel synthesis of 2-substituted 19-norvitamin D A-ring phosphine oxide from D-glucose as a building block

19-Norvitamin D A-ring phosphine oxide 5 was synthesized by a new sequence mode starting from D-glucose as a chiral template. Transformation of the pyranoside ring into the A-ring carbocycle was achieved by the Pd-catalyzed Ferrier rearrangement. The phosphine oxide 5 was obtained in an 18% overall yield by this novel cost-effective method.

Syntheses of specifically deoxygenated methyl α-isomaltotriosides

Specifically deoxygenated methyl α-isomaltotriosides were synthesized by the silver perchlorate-mediated condensation of a protected α-isomaltosyl chloride with suitably blocked derivatives of methyl α-D-glucopyranoside deoxygenated respectively at positi