252851-40-4

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 441044-62-8 methyl 6-S-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside 

Downstream Products

• 441044-63-9 methyl 2,3,4-tri-O-benzyl-6-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1-yl)-6-thio-α-D-glucopyranoside 
• 1112458-75-9 C₄₉H₅₆O₁₀S 
• 1377765-58-6 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4,-tri-O-benzyl-6-deoxy-6-thio-α-D-glucopyranoside 
• 1377765-55-3 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4,-tri-O-benzyl-6-deoxy-6-thio-α-D-glucopyranoside 
• 1448617-48-8 methyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-6-deoxy-6-thio-α-D-glucopyranoside 
• 1269658-10-7 C₅₆H₆₂O₁₀S₂ 
• 1020154-83-9 C₄₀H₄₆O₁₂S 
• 1020154-82-8 C₄₀H₄₆O₁₂S 
• 252851-44-8 methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-tridec-6-enopyranoside 
• 89160-13-4 methyl 8,12-anhydro-6,7-dideoxy-α-D-glycero-D-gulo-tridecopyranoside 
• 252851-42-6 methyl S,S-dioxo-2,3,4-tri-O-benzyl-6-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1-yl)-6-thio-α-D-glucopyranoside 
• 139195-45-2 (Z)-methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-tridec-6-enopyranoside 
• 565204-95-7 (3aS,4R,6S,6aR)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-[(E)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-furo[3,4-d][1,3]dioxole 

Relevant academic research and scientific papers

A Ramberg-Baecklund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids

Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Baecklund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Baecklund rearrangement is also reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Synthesis of S-linked carbohydrate analogues via a Ferrier reaction

In this work, the synthetic utility of the Ferrier reaction to access S-linked disaccharides and S-linked glycoamino acids has been probed. Significantly, entry to a range of 1,4- and 1,6-S-linked disaccharides has been achieved using glycals derived from glucose and galactose, and sulfur containing coupling partners derived from methyl α-d-glucopyranoside. Access to S-linked glycoamino acids and glycopeptides has also been achieved using protected cysteine and homocysteine coupling partners within the Ferrier reaction. Functionalisation of the Ferrier products, for example, via dihydroxylation using OsO4 or amino acid coupling, and deprotection of the targets have also been achieved. In this way, entry to materials of interest as mimics of biologically interesting disaccharides and glycopeptides has been realised, including targets derived from rare sugars such as talopyranose and gulopyranose.

Highly diastereoselective thioglycosylation of functionalized peracetylated glycosides catalyzed by MoO2Cl2

Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and β-(1→6)-S-linked-thiodisaccharide synthesis.

Ramberg - Backlund approaches to the synthesis of C-linked disaccharides

Readily available S-glycoside dioxides were utilized in a Ramberg- Backlund rearrangement for the construction of C-linked disaccharides. This approach is ideally suited to analogue synthesis simply by variation of the alkylating agent, and is illustrated