157903-84-9

Upstream product

• 106-95-6 allyl bromide 
• 161145-52-4 triphenyl(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)stannane 
• 157903-83-8 methyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 58341-63-2 methyl 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 58341-62-1 methyl 2-O-allyl-3-O-benzyl-α-D-glucopyranoside 
• 82659-52-7 1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 1011723-04-8 glucal epoxide 
• 2622-05-1 allylmagnesium bromide 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 374900-65-9 acetic acid 2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 

Downstream Products

• 184155-60-0 3-C-(3,4,6-tri-O-benzyl-α-D-arabino-hex-2-ulopyranosyl)propene 
• 320576-38-3 (2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol 
• 320576-39-4 2,6-anhydro-1,3,4-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-gulo-nonitol 
• 320576-36-1 (5R,7S,8S,9S,10R)-8,9-bis(benzyloxy)-7-[(benzyloxy)methyl]-1,6-dioxaspiro[4,5]decan-10-ol 
• 320576-34-9 (5S,7S,8S,9S,10R)-8,9-bis(benzyloxy)-7-[(benzyloxy)methyl]-1,6-dioxaspiro[4,5]decan-10-ol 
• 320576-37-2 (5R,7S,8S,9S,10R)-8,9-bis(benzyloxy)-7-[(benzyloxy)methyl]-1,6-dioxaspiro[4,5]decan-10-yl methanesulfonate 
• 320576-33-8 [[(5S,7S,8S,9S,10R)-8,9-bis(benzyloxy)-7-[(benzyloxy)methyl]-1,6-dioxaspiro[4,5]dec-10-yl]oxy](tert-butyl)dimethylsilane 
• 320576-32-7 [[(5R,7S,8S,9S,10R)-8,9-bis(benzyloxy)-7-[(benzyloxy)methyl]-1,6-dioxaspiro[4,5]dec-10-yl]oxy](tert-butyl)dimethylsilane 
• 320576-31-6 2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8-dideoxy-D-glycerol-L-gulo-nonitol 
• 374900-65-9 acetic acid 2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 1419172-63-6 (2R,3aR,5R,6S,7R,7aS)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-butyl-2-methyl-octahydropyrano[3,2-b]pyrrole 
• 1419172-64-7 (2R,3aR,5R,6S,7R,7aS)-1-benzyl-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-methyl-octahydropyrano[3,2-b]pyrrole 
• 1419172-67-0 (2R,3aR,5R,6S,7R,7aS)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-methyl-1-octyl-octahydropyrano[3,2-b]pyrrole 
• 1419172-68-1 (2R,3aR,5R,6S,7R,7aS)-6,7-bis(benzyloxy)-5-[(benzyloxy)-methyl]-1-hexyl-2-methyl-octahydropyrano[3,2-b]pyrrole 

Relevant academic research and scientific papers

Cytotoxic effects of C-glycosides in HOS and HeLa cell lines

Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI50 values) below 10 μM, the C-gluco

1,2-Migration of 2′-oxoalkyl group and concomitant synthesis of 2-C-branched O-, S-glycosides and glycosyl azides via 1,2-cyclopropanated sugars

Treatment of 2′-oxoalkyl 2-O-Ms(Ts)-α-C-mannosides (4, 5, and 6) with base resulted in 1,2-cyclopropanation via an intramolecular S N2 reaction due to their 1,2-trans-diaxial configurations. The 1,2-cyclopropanated sugars (10 and 13) were react

From α-1,2-Anhydrosugars to C-Glycosides: The Influence of Lewis Acids and Nucleophiles on the Stereochemistry

Ring opening of the epoxide function in α-1,2-anhydrosugars with alkynyl zinc and titanium compounds proceeds with retention of configuration to afford α-C-alkynylglycosides in reasonable to good yields, while the use of the corresponding alkynyltrifluoroborates results in the formation α/β mixtures. Vinyl nucleophiles predominantly afford α-products, whereas allyl and allenyl species almost exclusively yield β-C-glycosides.

Epimerization of 2'-carbonylalkyl-C-glycosides via enolation, beta-elimination and intramolecular cycloaddition.

Treatment of 2'-carbonyl-alpha-C-glycopyranosides of gluco, galacto, manno, 2-deoxy, and 2-azido sugars with 4% NaOMe resulted in anomeric epimerization to give their respective beta-anomers in good to excellent yields. The epimerization of the 2'-aldehyd

Multifunctionalized α,β-cyclopentenones from C-2 and C-4-ulopyranosyl compounds: A stereospecific rearrangement initiated by base

Base treatment of O-benzyl protected C-2- or C-4-ulopyranosyl compounds (4α, 4β, and 11) by either 10% Et3N or 1% K2CO3 in MeOH initiated a β elimination to afford α,β-unsaturated C-ulopyranosyl compounds (5α, 5β, and 12), which further rearranged in a stereocontrolled manner to multifunctionalized α,β-cyclopentenones (6 and 14) in 70-80% yield. Both C-α- and C-β-2-ulosides (5α and 5β) produced the same cyclopentenone 6, indicating that a 1,2-enolate is formed prior to the cleavage of the C-5-O bond. Because 6 is racemic, it was probably formed by the intramolecular cycloaldolization of two equally populated enantiomeric intermediates. When treated with 90% Et3N in MeOH, 5α yielded almost exclusively 15 (isomer of 6), which was formed by a migration of the double bond in 5α during the previously described rearrangement. Thus either 6 or 15 was the major product, depending on the base used.

Synthesis and Stereochemical Confirmation of the cis-Fused L/M and N/O Ring Systems of Maitotoxin

Stereocontrolled synthesis of cis-fused 1,6-dioxadecalin system 1, which corresponds to the L/M and N/O rings of maitotoxin, was accomplished.Comparison of its (1)H and (13)C NMR data with those of the natural toxin established the earlier stereochemical

Preparation and transmetallation of a triphenylstannyl β-D-glucopyranoside: A highly stereoselective route to β-D-C-glycosides via glycosyl dianions

The triphenylstannyl β-D-glucopyranoside 4 was synthesized in one step from the 1,2-anhydro-α-D-glucopyranose 3 with (triphenylstannyl)lithium. Transmetallation of 4 with excess BuLi, followed by quenching the dianion 7 with CD3OD gave (IS)-1,5-anhydro-3,4,6-tri-o-benzyl-[1-2H]-D-glucitol (8) in 81% yield. Trapping of 7 with benzaldehyde, isobutyraldehyde, or acroleine gave the expected β-D-configurated products 11, 12, and 13 in good yields. Preparation of C-acyl glycosides from acid chlorides, such as acetyl or benzoyl chloride was not practicable, but addition of benzonitrile to 7 yielded 84% of the benzoylated product 14. Treatment of 7 with MeI led to 15 (30%) along with 40% of 18, C-alkylation being accompanied by halogen-metal exchange. Prior addition of lithium 2-thienylcyanocuprate increased the yield of 15 to 50% and using dimethyl sulfate instead of MeI led to 77% of 15. No α-D-anomers could be detected, except with allyl bromide as the electrophile, which yielded in a 1:1 mixture of the anomers 16 and 17.