87470-75-5

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 27891-73-2 phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside 
• 618-31-5 benzylidene dibromide 
• 100-52-7 benzaldehyde 
• 108-98-5 thiophenol 
• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 
• 3616-19-1 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 
• 4551-15-9 phenylthiotrimethylsilane 
• 5346-81-6 phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 4753-07-5 α-hepta-O-acetylmaltosyl bromide 
• 309913-14-2 Phenyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glycopyranosyl)-1-thio-β-D-glucopyranoside 

Downstream Products

• 244286-77-9 phenyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 309913-15-3 Phenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside 
• 309913-14-2 Phenyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glycopyranosyl)-1-thio-β-D-glucopyranoside 
• 259742-19-3 phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-1^I-thio-β-maltoside 
• 259742-12-6 phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-(2-carboxybenzoyl)-1^I-thio-β-maltoside 
• 259742-11-5 phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-tert-butyldiphenylsilyl-1^I-thio-β-maltoside 
• 478549-14-3 phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-[(benzotriazol-1-yloxy)-2-carbonylbenzoyl]-1^I-thio-β-maltoside 
• 250335-04-7 Phenyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 250335-03-6 Phenyl 2,3-di-O-benzyl-6-O-(4-phenylbenzoyl)-4-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 309913-16-4 Phenyl 2,3-di-O-benzyl-6-O-bromoacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 309913-20-0 Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 309913-21-1 Phenyl 2,3-di-O-benzyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-6-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside 
• 171356-78-8 Methyl O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Indirect and direct approaches in the synthesis of a new mono-6-O-benzyl methylated γ-cyclodextrin as chiral selector for enantioselective gas chromatography

6I-O-Benzyl-2I-VIII, 3I-VIII, 6II-VIII-tricosa-O-methyl-γ-cyclodextrin was synthesized using indirect and direct approaches. The first indirect strategy consists of a multi-step sequence including the ring opening of the permethylated α-cyclodextrin, elongation of the chain with a 6-O-benzyl methylated disaccharide derivative, and macrocyclization. The direct method deals with a selective mono-6-O-TBDMS protection, permethylation, deprotection, and benzylation sequence of γ-cyclodextrin. The results clearly show the higher efficiency of the direct approach but demonstrate the feasibility of the insertion of a modified maltose derivative (indirect method). The new mono-6-O-modified methylated γ-cyclodextrin was used as a selector for the preparation of the new chiral stationary phase. Preliminary enantioselective gas chromatography applications are also reported.

A facile protocol for direct conversion of unprotected sugars into phenyl 4,6-O-benzylidene-per-O-acetylated-1,2-trans-thioglycosides

A short and practical methodology for conversion of unprotected D-glucose, maltose, cellobiose and lactose into the corresponding phenyl 4,6-O-benzylidine-per-O-acetylated-1,2-trans-thioglycosides is described. The protocol is based on the execution of five reaction steps (bromoacetylation, thiophenolysis under phase transfer catalysis conditions, deacetylation, benzylidenation and acetylation) in one continuous procedure and provides a fast access to the title compounds as pure crystalline products without chromatographic purification.

Chemical synthesis of cyclodextrins by using intramolecular glycosylation

An efficient synthesis of cyclodextrins (CDs) by using the intramolecular glycosylation is demonstrated. α-CD, an α(1→4)linked hexaglucoside, was prepared via a block condensation of three maltose units. A modified key maltose intermediate as a precursor to both glycosyl donor and acceptor components was prepared in 6 steps starting from maltose. All the glycosylation for chain elongation and cyclization of saccharides was carried out after tethering the donor to the acceptor by the phthaloyl bridge to give the desired saccharides in good yields with complete α-selectivity. δ-CD composed of 9 glucose units was synthesized by the same manner from three maltotriose units.

New phenyl 6,4'-substituted-1-thio-β-maltosides, building blocks for the synthesis of linear and branched malto-oligosaccharides

An efficient strategy to synthesize a number of new phenylthio-maltoside derivatives in yields from 55 to 95% is described. These derivatives can be used as suitable building blocks for stepwise synthesis of starch derived malto-oligosaccharides.

Direct synthesis of pseudo-disaccharides by rearrangement of unsaturated disaccharides

The series of unsaturated disaccharides 10-14 undergo stereoselective reductive rearrangement with TIBAL (triisobutylaluminium) to afford (1→4) and (1→6) ether-linked pseudo-disaccharides 2-9.

Novel molecular clamp method for anomeric stereocontrol of glycosylation

Stereocontrolled glycosylation is described by using a molecular clamp, which binds a glycosyl donor to an acceptor and controls their spatial arrangement. An α(1→4) glycosidic linkage was formed in a good yield with high selectivity by the use of a phthaloyl bridge bound to both 6-positions of a glycosyl donor and an acceptor. β-Selective glycosylation was effected by the use of a silyl bridge attached to the same 6-positions of the same glycosyl donor and acceptor. Application of this method to the synthesis of a maltotetraose derivative is also described.