68366-59-6

Upstream product

• 91685-06-2 methyl 2-O-benzoyl-4, 6-O-benzylidene-α-D-mannopyranoside 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 86420-70-4 methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 98-88-4 benzoyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 613-90-1 benzoyl cyanide 

Downstream Products

• 136919-88-5 Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-cyano-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 118117-23-0 methyl-2-O-benzoyl-3-vinyl-4,6-O-benzylidene-α-D-allopyranoside 
• 80018-90-2 methyl 3-C-benzyl-4,6-O-benzylidene-α-D-allopyranoside 
• 68325-67-7 Methyl 2,4,6-Tri-O-benzoyl-α-D-ribo-hexopyranosid-3-uloside 
• 108947-20-2 Methyl-2-O-benzoyl-4,6-O-benzyliden-2-C-2-methyl-α-D-ribo-hexopyranosid-3-ulose 
• 80018-95-7 methyl 3-C-allyl-4,6-O-benzylidene-α-D-allopyranoside 
• 191024-62-1 Benzoic acid (2R,4aR,6S,7R,8aS)-8-difluoromethylene-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 488820-54-8 methyl 2,3''-anhydro-4,6-O-benzylidene-3-C-[(Z)-(hydroxymethyl)methylene]-α-D-ribo-hexopyranoside 
• 488820-53-7 methyl 4,6-O-benzylidene-3-C-[(Z)-(hydroxymethyl)methylene]-α-D-ribo-hexopyranoside 
• 191024-65-4 (2R,4aR,6S,7R,8aS)-8-[1-Fluoro-meth-(Z)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 191024-67-6 (2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-8-trifluoromethyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine 
• 205688-37-5 Benzoic acid (2S,3R,6S)-6-hydroxymethyl-2-methoxy-4-trifluoromethyl-3,6-dihydro-2H-pyran-3-yl ester 
• 191024-63-2 Benzoic acid (2R,4aR,6S,7R,8R,8aS)-8-difluoromethyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 

Relevant academic research and scientific papers

Wittig Reaction: Domino Olefination and Stereoselectivity DFT Study. Synthesis of the Miharamycins' Bicyclic Sugar Moiety

2-O-Acyl protected-d-ribo-3-uloses reacted with [(ethoxycarbonyl)methylene]triphenylphosphorane in acetonitrile to afford regio- and stereoselectively 2-(Z)-alkenes in 10-60 min under microwave irradiation. This domino reaction is proposed to proceed via tautomerization of 3-ulose to enol, acyl migration, tautomerization to the 3-O-acyl-2-ulose, and Wittig reaction. Alternatively, in chloroform, regioselective 3-olefination of 2-O-pivaloyl-3-uloses gave (E)-alkenes, key precursors for the miharamycins' bicyclic sugar moiety.

Scalable synthesis of a mycosamine donor. Overcoming difficult reactivity in allose systems

Mycosamine is a dideoxyaminosugar found in medicinally relevant macrolides, including amphotericin B and nystatin. Herein we report a reliable, high yielding, scalable synthesis of a mycosamine donor. A major goal of our approach was to minimize purificat

Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols

Synthesis of 10-membered bislactones by PCC oxidation of methyl 2,6-di-O-pivaloyl-α-D-glucopyranoside and methyl 4,6-O-benzylidene- α-D-glucopyranoside is described, with emphasis on their structure elucidation using the information gained by combination

Construction of a branched chain at C-3 of a hexopyranoside. Synthesis of miharamycin sugar moiety analogs

Synthesis of the conveniently protected epimer at C-3' of the miharamycin sugar moiety was accomplished starting from the corresponding 3,3'-spiroepoxide. Reaction of the epoxide with lithium cyanide, followed by hydrolysis and spontaneous cyclization, af

Highly stereoselective route to aldol products incorporating fluorine containing methyl groups starting from a single D-glucose-derived intermediate

Chiral aldol structures with fluorine modifications on a methyl group have been realized by utilization of the relatively rigid cyclic intermediates from the very common chiral pool compound, D-glucose, leading to attainment of the high diastereoselectivi

Stereospecific synthesis of branched-chain sugars by a novel aldol-type cyclocondensation

A procedure for the preparation of branched-chain sugars having highly functionalised C-branches is reported.Reaction of furanos-3-uloses, pyranos-3-uloses, or pyranos-2-uloses with sodium cyanide followed by mesylation of the corresponding cyanohydrin af

PREPARATION AND DIELS-ALDER REACTIONS OF A PYRANOID VINYL GLYCAL: MODEL STUDIES FOR ANTHRAQUINONE AGLYCONE AND CARBOHYDRATE SYNTHESES

The preparation of a conjugated pyranoid vinyl glycal is reported, along with several of its thermal cycloaddition reactions with a variety of dienophiles.Applications to the anthraquinone antitumor agents are discussed.

Enolates of carbohydrates, 5. Syntheses of axially methyl-branched pyranosiduloses

The α-C-methylated carbohydrates 3 and 5 are available from the benzoyl- and benzylidene protected 2- and 3-uloses 1a, 2, and 4 by reaction with potassium tert-butoxide/methyl iodide in N,N-dimethylformamide.Under pthe same conditions the 2-O-benzyl-3-ulose 1b yields the enol ether 6a, and the enolone 8 is obtained from the 2-O-benzoyl-3-ulose 7.

Arylazo-glycenosides. Part 8. Synthesis and Reactions of Some 2- and 3-Arylazo-derivatives of Methyl 4,6-O-Benzylidene-2,3-dideoxy-D-threo-hex-2-enopyranosides

Preparations are described of the α- and β-anomers of methyl 4,6-O-benzylidene-2,3-dideoxy-2-phenylazo-D-threo-hex-2-enopyranoside and of methyl 4,6-O-benzyliden-2,3-dideoxy-3-phenylazo-α-D-threo-hex-2-enopyranoside using D-galactose as the initial materi

Branched-chain Sugars. XXIV. Synthesis of Methyl 6-Deoxy-3-C-methyl-β-D-gulopyranoside (Methyl β-Virenoside)

Methyl 6-deoxy-3-C-methyl-β-D-gulopyranoside (methyl β-virenoside) was prepared from D-galactose.An attempted synthesis of the virenoside by the inversion at C-4 of methyl 6-deoxy-3C-methyl-α-D-allopyranoside was unsuccessful.