65530-28-1

Upstream product

• 100-52-7 benzaldehyde 
• 26922-85-0 Methyl 3-deoxy-α-D-ribo-hexopyranoside 
• 157130-84-2 Methyl 4,6-O-benzylidene-2-O-butyryl-3-deoxy-α-D-ribo-hexopyranoside 
• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 138513-06-1 methyl 4,6-O-benzylidene-2,3-O-thiocarbonyl-α-D-glucoside 
• 85716-67-2 methyl 2,3-anhydro-4,6-O-benzylidene-2-nitro-α-D-mannopyranoside 
• 24332-89-6 methyl-(α-D-lyxo-3-deoxy-hexopyranoside) 
• 2880-96-8 methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-talopyranose 
• 16697-40-8 methyl-[O⁴,O⁶-((S)-benzylidene)-S-methyl-3-thio-β-D-idopyranoside] 
• 86420-78-2 methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside 
• 2880-96-8 (1aR,2S,6R,7aR,7bR)-2-Methoxy-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene 
• 192769-47-4 C₁₅H₁₇ClO₆S 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 74524-02-0 methyl 4,6-O-(phenylmethylene)-3-deoxy-α-D-erythro-hexopyranoside-2-ulose 

Downstream Products

• 79297-68-0 methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-deoxy-α-D-ribo-hexopyranoside 
• 138663-51-1 methyl-[O⁴,O⁶-((R)-benzylidene)-O²-methyl-α-D-ribo-3-deoxy-hexopyranoside] 
• 138665-01-7 Methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-ribo-hexopyranoside 
• 26922-84-9 methyl 4-O-benzyl-3-deoxy-α-D-ribo-hexopyranoside 
• 1352406-78-0 methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside 
• 1352406-79-1 methyl 2-O-(p-methoxybenzyl)-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside 
• 1352406-80-4 methyl 4-O-benzyl-3-deoxy-α-D-gluco-hexodialdo-1,5-pyranoside 
• 100-51-6 benzyl alcohol 
• 56405-85-7 methyl-[O⁴,O⁶-((S)-benzylidene)-O²-methyl-α-D-lyxo-3-deoxy-hexopyranoside] 
• 56405-85-7 methyl-[O⁴,O⁶-((S)-benzylidene)-O²-methyl-β-D-lyxo-3-deoxy-hexopyranoside] 
• 145149-83-3 Methyl 2,4-di-O-benzyl-3-deoxy-α-D-ribo-hexopyranoside 
• 117371-67-2 Methyl 2,6-di-O-benzyl-3-deoxy-α-D-ribo-hexopyranoside 
• 581060-39-1 (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-2'-(4-methoxybenzyloxy)-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane 
• 905312-31-4 (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-2'-(4-methoxybenzyloxy)-1'-(p-toluenesulfonyloxy)propyl]-4-vinylcyclohexan-2-ol 

Relevant academic research and scientific papers

Synthesis of locked pyranosyl nucleic acid (LpNA)

A new locked pyranosyl nucleoside was synthesized by phenylsulfinyl- assisted chemistry. The novel building block was inserted into oligonucleotides and provides new insight on conformational restricted pyranosyl nucleosides on duplex formation

Preparation of 2-C- and 3-C-cyano-2-enopyranoside derivatives and their epoxidation

Methyl 4,6-O-benzylidene-2-C- and 3-C-cyano-2,3-dideoxy-d-erythro-hex-2-enopyranosides and -2-enitols were prepared and their epoxidation was performed.

New synthesis of (-)- and (+)-actinobolin from D-glucose

The total synthesis of (-)-actinobolin 2, an antipode of the natural product starting from D-glucose is described. A three-component coupling reaction of a functionalized cyclohexenone (+)-6, derived from D-glucose by way of Ferrier's carbocyclization, wi

Novel and convenient method for the syntheses of 2,6-dideoxypyranoses, 3,6-dideoxypyranoses, and azido (amino) analogs of 3,6-dideoxypyranoses

A novel method of regioselective deoxygenation of methyl 4,6-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside, and its application for the syntheses of 2,6-dideoxypyranoses, 3,6-dideoxypyranoses, and azido (amino) analogs of 3,6-dideoxypyranoses were reported.

Studies of the stereoselective reduction of ketosugar (hexosulose)

The results from the studies of the stereoselective reduction of ketosugar (hexosulose) were reported. Combining our results and those reported in the literature, we summarize the factors in controlling the stereoselective reduction of ketosugars. These findings are valuable in the synthesis of various carbohydrate derivatives.

Thio-sugars III. Radical catalyzed thione-thiol rearrangement of cyclic thionocarbonates on a pyranose ring: Formation of cis-arranged cyclic thiolcarbonates

Pyranoside 3,4-cis-thionocarbonates, under radical-promoted reaction conditions (method A, B, or C, described in the text), gave O-S rearrangement products, 3,4-thiolcarbonates of cis-stereochemistry, in acceptable yields. 2,3-Thionocarbonates of trans-stereochemistry also gave the rearrangement products of cis-stereochemistry preferentially in method B (photolysis with hexabutyldistannane). Although regio-control of the product was not satisfactory in most cases, some of the results suggested that the regioselectivity of the reaction is markedly influenced by the stereochemistry of the anomeric position of the substrates. The products were converted to thioglycosides (peracetate forms) by conventional means.

SYNTHESIS OF METHYL α-d-ALLOPYRANOSIDE AND METHYL α-D-Ribo-HEXOPYRANOSIDE: A CONVENIENT CHEMOENZYMATIC APPROACH

An efficient chemoenzymatic synthesis of methyl α-D-allopyranoside and methyl 3-deoxy-α-D-ribo-hexopyranoside starting from methyl 4,6-O-benzylidene-α-D-glucopyranoside is described.

Selective generation of free radicals from epoxides using a transition-metal radical. A powerful new tool for organic synthesis

Bis(cyclopentadienyl)titanium(III) chloride reacts with epoxides by initial C-O homolysis. The regiochemistry of the opening is determined by the relative stabilities of the radicals. Depending on the reaction partners, these radicals undergo intramolecular (hex-5-enyl cyclization) or intermolecular additions to olefins. The resultant radicals are efficiently scavenged by a second equivalent of Ti(III) to afford the corresponding Ti(IV) derivative. Treatment of this intermediate with electrophiles such as H+ or halogens provides a route to functionalized cyclopentanes and other useful products. The radical initially formed from an epoxide can also be trapped by H-atom donors such as 1,4-cyclohexadiene or tert-butyl thiol, resulting in an overall reduction of the epoxide. In the absence of a H-atom donor or an olefin, this radical is trapped by Ti(III), resulting in a β-oxido-Ti organometallic species which undergoes facile elimination to give an olefin. The reaction conditions are remarkably mild and are applicable to very sensitive substrates.