161275-25-8

Upstream product

• 106-95-6 allyl bromide 
• 161145-52-4 triphenyl(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)stannane 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 193546-84-8 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene 
• 81972-19-2 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene 
• 107-05-1 3-chloroprop-1-ene 
• 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 
• 1730-25-2 allylmagnesium bromide 
• 2622-05-1 allylmagnesium bromide 
• 24850-33-7 allyltributylstanane 
• 192929-28-5 (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran 

Downstream Products

• 81972-19-2 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene 
• 212395-00-1 Formic acid (2S,3S,4S,5R,6R)-2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 192929-28-5 (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran 
• 252202-48-5 3-(2'-O-prop-1-enyl-3',4',6'-tri-O-benzyl-β-D-glucopyranosyl)prop-1-ene 
• 263388-36-9 (2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((R)-1-phenoxy-allyloxy)-tetrahydro-pyran 
• 288584-96-3 3-C-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)1-propanol 
• 320576-39-4 2,6-anhydro-1,3,4-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-gulo-nonitol 
• 909533-56-8 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-cyclopropylmethyl-tetrahydro-pyran-3-ol 
• 1015481-45-4 ((2S,3S,4S,5R,6R)-2-allyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane 
• 115184-49-1 3,4,6-tri-O-benzyl-β-D-glucopyranose 
• 192929-31-0 3-C-(3,4,6-tri-O-benzyl-β-D-arabino-hex-2-ulopyranosyl)propene 
• 193546-84-8 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene 
• 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 

Relevant academic research and scientific papers

A Short Sequence for the Iterative Synthesis of Fused Polyethers

A simple and efficient four-step sequence for the synthesis of fused polyether arrays has been developed. Cyclic ethers are installed by sequential alkynyl ether formation, carbocupration, ring-closing metathesis and hydroboration with acidic workup. Cruc

Synthesis of fused pyran-carbahexopyranoses as glycosidase inhibitors

Synthesis of polyhydroxylated oxabicyclo[4,4,0]decanes, which constitute a new family of annulated carbasugars, has been accomplished in a stereoselective manner by employing readily available 1,2-anhydro-3,4,6-tri-O-benzyl-α-d-glycopyranoses.

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

Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled

Zinc-mediated synthesis of α-C-glycosides from 1,2-anhydroglycosides

α-C-Glycosides have been prepared by the addition of organozinc reagents to glycal epoxides. Dialkyl and diaryl zinc reagents in the presence of CF3COOH provide the corresponding α-glycosides in 53-82% yields. Organozinc chlorides RZnC1 formed

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.

C-Glycosides to fused polycyclic ethers

This manuscript describes the synthesis of fused polycyclic ethers from the coupling of C-glycoside forming reactions with ring closing metathesis and acid mediated annulation reactions.

Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C

Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis.

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.