68027-34-9

Upstream product

• 84207-56-7 6-O-<(3'R,4'R,5'R)-5'-hydroxy-3',4',6'-tribenzyloxyhex-1'(Z)-enyl>-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 244282-14-2 (3aR,5R,5aS,8aS,8bR)-5-[1-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-1-methyl-ethoxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 350985-71-6 phenyl 3,4,6-tri-O-benzyl-2-O-(1-para-methoxyphenylethenyl)-1-thio-β-D-glucopyranoside 
• 451463-10-8 (Z)-2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride 
• 1197820-03-3 2-methoxy-2-(S)-phenyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (R)-S-oxide 
• 1359734-73-8 C₃₃H₃₈O₇S 
• 84207-56-7 6-O-<(3'R,4'R,5'R)-5'-hydroxy-3',4',6'-tribenzyloxyhex-1'(E)-enyl>-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 301645-79-4 methyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 55659-53-5 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-d-glucopyranose 
• 455928-97-9 methyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 350985-70-5 phenyl 3,4,6-tri-O-benzyl-2-O-para-methoxybenzoyl-1-thio-β-D-glucopyranoside 
• 152871-96-0 phenyl 1-deoxy-2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 127299-77-8 Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Protecting Group Dependence of Stereochemical Outcome of Glycosylation of 2-O-(Thiophen-2-yl)methyl Ether Protected Glycosyl Donors

A series of glycosyl donors possessing a (thiophen-2-yl)methyl ether protecting group at position 2 were synthesised and the effect of the protecting group pattern of other hydroxyls on the stereochemical outcome of glycosylation was investigated. Studies revealed optimal α-selectivity for glycosylation using a fully armed tri-benzylated donor, whilst other protecting group patterns were significantly less effective. Low-temperature NMR studies of both fully armed and fully disarmed donors revealed the intermediacy of cyclised sulfonium ion intermediates. Reaction conditions were developed which allowed removal of the (thiophen-2-yl)methyl ether protecting group either selectively, or together with benzyl ethers. Glycosyl donors with a 2-O-thiophenylmethyl ether protecting group undergo six-membered ring NGP, as demonstrated by low-T NMR studies, but the stereochemical outcome of glycosylation is highly dependent on other protecting groups.

Neighbouring group participation during glycosylation: Do 2-substituted ethyl ethers participate?

The development of new protecting groups that undergo neighbouring group participation (NGP) via six-membered ring intermediates to promote the formation of α-1,2-cis glycosidic linkages complements the established use of 5-ring NGP in terms of stereochem

Stereoselective glycosylations using oxathiane spiroketal glycosyl donors

Novel oxathiane spiroketal donors have been synthesised and activated via an umpolung S-arylation strategy using 1,3,5-trimethoxybenzene and 1,3-dimethoxybenzene. The comparative reactivity of the resulting 2,4,6-trimethoxyphenyl (TMP)- and 2,4-dimethoxyp

Do glycosyl sulfonium ions engage in neighbouring-group participation? A Study of oxathiane glycosyl donors and the basis for their stereoselectivity

Neighbouring-group participation has long been used to control the synthesis of 1,2-trans-glycosides. More recently there has been a growing interest in the development of similar strategies for the synthesis of 1,2-cis-glycosides, in particular the use of auxiliary groups that generate sulfonium ion intermediates. However, there has been some debate over the role of sulfonium ion intermediates in these reactions: do sulfonium ions actually engage in neighbouring-group participation, or are they a resting state of the system prior to reaction through an oxacarbenium ion intermediate? Herein, we describe the reactivities and stereoselectivities of a family of bicyclic thioglycosides in which an oxathiane ring is fused to the sugar to form a trans-decalin-like structure. A methyl sulfonium ion derived from one such glycosyl donor is so stable that it can be crystallised from ethanol, yet it reacts with complete stereoselectivity at high temperature. The importance of a ketal group in the oxathiane ring for maintaining this high stereoselectivity is investigated using a combination of experiment and ab initio calculations. The data are discussed in terms of SN1 and SN2 type mechanisms. Trends in stereoselectivity across a series of compounds are more consistent with selective addition to oxacarbenium ions rather than a shift between SN1 and SN2 mechanisms. Copyright

Stereoselective glycosylation using oxathiane glycosyl donors

A bicyclic glycosyl donor is activated as an arylsulfonium ion and used to synthesise α-glycosides with high stereoselectivity.

Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD

(Chemical Equation Presented) Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary

Allyl protecting group mediated intramolecular aglycon delivery (IAD) of glycosyl fluorides

Stereospecific 1,2-cis-glycosylation of 2-O-allyl protected glucosyl and mannosyl fluorides can be achieved via a sequence of allyl isomerization, N-iodosuccinimide mediated tethering, and intramolecular aglycon delivery (IAD). Fluoride is advantageous as

Stereoselective 1,2-cis glycosylation of 2-O-Allyl protected thioglycosides

The technique of intramolecular aglycon delivery (IAD), whereby a glycosyl acceptor is temporarily appended to a hydroxyl group of a glycosyl donor is an attractive method that can allow the synthesis of 1,2-cis glycosides in an entirely stereoselective f

N-Iodosuccinimide-mediated intramolecular aglycon delivery

Enol ethers may be accessed via Tebbe methylenation of either 2-O acetates or para-methoxybenzoates. N-Iodosuccinimide may then be employed to achieve both tethering and thioglycoside activation allowing the stereoselective synthesis of α-glucosides and β-mannosides, either in a one or two step procedure.

Stereospecific synthesis of 1,2-cis glycosides by allyl-mediated intramolecular aglycon delivery. 2.The use of glycosyl fluorides.

[reaction: see text] Stereospecific 1,2-cis glycosylation of 2-O-allyl-protected glucosyl and mannosyl fluorides via a sequence of allyl isomerization, N-iodosuccinimide-mediated tethering, and intramolecular aglycon delivery (IAD) is reported. The use of