193546-84-8

Upstream product

• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 1011723-04-8 glucal epoxide 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 55628-56-3 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 762-72-1 allyl-trimethyl-silane 
• 108-24-7 acetic anhydride 
• 161275-25-8 3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene 

Downstream Products

• 212395-03-4 (2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methyl-2,3,4,4a,8,8a-hexahydro-pyrano[3,2-b]pyran 
• 212395-05-6 Acetic acid (2S,3R,4aS,6R,7R,8S,8aS)-2-allyl-7,8-bis-benzyloxy-6-benzyloxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-yl ester 
• 212395-07-8 (2R,3S,4aS,6R,7R,8S,8aS)-2-Allyl-7,8-bis-benzyloxy-6-benzyloxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol 
• 212395-08-9 (2S,3R,4aS,6R,7R,8S,8aS)-2-Allyl-7,8-bis-benzyloxy-6-benzyloxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol 
• 192929-31-0 3-C-(3,4,6-tri-O-benzyl-β-D-arabino-hex-2-ulopyranosyl)propene 
• 440362-88-9 Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-triisopropylsilanyloxy-propyl)-tetrahydro-pyran-3-yl ester 
• 440362-89-0 (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-but-3-enyl-5-isopropenyloxy-tetrahydro-pyran 
• 440362-87-8 (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-butenyl)-tetrahydro-pyran-3-acetate 
• 440362-97-0 Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-oxo-propyl)-tetrahydro-pyran-3-yl ester 
• 440362-96-9 Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester 
• 161275-25-8 3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene 
• 212395-02-3 (2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-3-isopropenyloxy-tetrahydro-pyran 

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

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.

The synthesis of some epoxyalkyl β-C-glycosides as potential inhibitors of β-glucan hydrolases

The treatment of tetra-O-benzyl-D-glucono-1,5-lactone with various alkenylmagnesium halides gave the intermediate lactols which, upon reduction (Et3SiH/BF3) and protecting group manipulation, yielded alkenyl tetra-O-acetyl-β-D-C-gluc