79241-07-9

Upstream product

• 68144-11-6 1,4-anhydro-2-deoxy-5,6-O-isopropylidene-D-arabino-hex-1-enitol 
• 100-39-0 benzyl bromide 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 1017236-05-3 (2R,3R,4R,5R)-1,2-O-isopropylidene-3,6-anhydro-4-O-benzyl-5-O-methanesulfonyl-D-glucitol 
• 1167439-17-9 C₁₆H₂₁IO₄ 
• 6160-67-4 (3aS,4R,6R,6aS)-4-chloro-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 17087-84-2 (3aS,4R,6R,6aS)-4-chloro-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 530-26-7 D-Mannose 
• 68144-11-6 1,4-anhydro-2-deoxy-5,6-O-isopropylidene-D-arabinohex-1-enitol 
• 7757-38-2 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 

Downstream Products

• 112289-64-2 1-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-5,6-O-isopropylidne-α-D-glucofuranose 

Relevant academic research and scientific papers

Synthesis of Bioactive Side-Chain Analogues of TAN-2483B

The fungal metabolite TAN-2483B has a 2,6-trans-relationship across the pyran ring of its furo[3,4-b]pyran-5-one core, which has thwarted previous attempts at its synthesis. We have now developed a chiral pool approach to this core and prepared side-chain

Synthesis of enantiomerically pure highly functionalized furanoid glycal and 2,5-Dihydrofuran building blocks

Differently protected enantiomerically pure furanoid glycals (5a-d) and highly functionalized 2,5-dihydrofurans (6a-b) were synthesized from their respective 2,3,4-trisubstituted tetrahydrofurans. These furanoid glycals were identified as 1,4-anhydro-2-de

Norrisolide: Total synthesis and related studies

A stereoselective synthesis of (+)-norrisolide is presented. This natural product belongs to a family of marine spongiane diterpenes the structure of which is characterized by a fused γ-lactone-γ-lactol ring system attached to a bicyclic hydrophobic core.

Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using overman rearrangement as the key reaction

Total synthesis starting from aldohexoses of naturally occurring α-substituted α-amino acids, (+)-myriocin (1) and (-)-sphingofungin E (2), is described. Overman rearrangement of allylic trichloroacetimidate 6E derived from D-mannose effectively generated the tetrasubstituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized moiety 3 of myriocin stereoselectively. Sulfone-mediated coupling reaction of the allyl bromide 3 with C12 hydrophobic part 4 successfully constructed the carbon framework possessing E-olefin 28. Removal of the sulfone and protecting groups completed the chiral and stereoselective total synthesis of (+)-myriocin (1). A similar transformation starting from D-glucose also accomplished the total synthesis of (-)-sphingofungin E (2).

Synthetic studies on norrisolide: Enantioselective synthesis of the norrisane side chain

Norrisolide (1) belongs to a family of marine diterpenes that are characterized by the assembly of a bicyclic core with a unique and highly oxygenated side chain (norrisane side chain). As a prelude to the synthesis of 1, we present herein a short, effici

Synthesis of 2'-deoxy-2'-phenylselenenyl-furanosyl nucleosides from glycals using electrophilic selenium reagents. Conversion into 2'-deoxynucleosides

2'-Deoxy-2'-phenylselenenyl-furanosyl nucleosides have been synthesized stereoselectively from glycals using selenium reagents, and converted into 2'-deoxynucleosides by treatment with tributyltin hydride. Some of the factors which affect the stereoselectivity of the reaction are the stereochemistry at position 3, the nature of the protecting groups, the phenylselenenyl reagent and the solvent.

SELENIUM-CONTROLLED STEREOSELECTIVE SYNTHESIS OF 2'-DEOXYNUCLEOSIDES FROM GLYCALS. A FORMAL SYNTHESIS OF AZT

2'-Deoxynucleosides have been stereoselectively synthesized starting from glycals, using phenylselenyl reagents.Key Words: 2'-Deoxynucleosides, stereoselective glycosylation, glycals.

REACTION OF ACETYL HYPOFLUORITE WITH PYRANOID AND FURANOID GLYCALS

The regiospecific syn-addition of acetyl hypofluorite to glycals derived from pentopyranoses led to mixtures of stereoisomers.Stereospecific reactions occured with furanoid glycals, the direction of addition being governed by the nature of the substituent at C-3.Whereas a benzyloxy group caused attack from the opposite, less-hindered face of the double bond, a hydroxyl group induced addition from the same side.From these reactions, 2-deoxy-2-fluoro derivatives of β-D-arabino-, α-D-ribo-, β-D-lyxo-, and α-D-xylo-pyranose as well as β-D-manno-, α-D-guco-, α-D-ribo-, and β-D-arabino-furanose were obtained; their 1H-, 13C-, and 19F-n.m.r. data are given.