72471-11-5

Upstream product

• 76679-47-5 methyl-2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-α-D-glucopyranoside 
• 73111-13-4 Methanesulfonic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 114219-26-0 methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside 
• 19139-89-0 (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 82231-38-7 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 674302-87-5 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-(4,5,6,7-tetrachlorophthalimid-2-yl)-α-D-glucopyranoside 

Downstream Products

• 152581-76-5 [1-Methyl-piperidin-(2E)-ylidene]-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-amine 
• 148915-23-5 methyl 6-deoxy-6-nitro-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 210479-91-7 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-(tert-butoxycarbonylamino-methyl)-5-[((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1000865-12-2 methyl 6-amino-2,3,4-tri-O-benzyl-6-deoxy-6-N-(2-nitrobenzenesulfonyl)-α-D-glucopyranoside 
• 1000865-11-1 methyl 6-amino-2,3,4-tri-O-benzyl-6-deoxy-6-N-(trifluoromethanesulfonyl)-α-D-glucopyranoside 
• 887624-14-8 bis(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl)amine 
• 887624-16-0 (R)-12-Hydroxy-octadecanoic acid bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-amide 
• 887624-19-3 Hexanoic acid (R)-11-[bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-1-hexyl-undecyl ester 
• 1063748-64-0 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-[(N'-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)ureido]-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthetic entry to functionalised morpholines and [1,4]-oxazepanes via reductive amination reactions of carbohydrate derived dialdehydes

Synthetic entry to functionalised morpholines and [1,4]-oxazepanes by reductive amination reactions between amines and carbohydrate derived dialdehydes is described. The rapid synthesis of functionalised morpholines and [1,4]-oxazepanes displaying up to three stereocentres, by reductive amination reactions between carbohydrate derived dialdehydes and a range of amines, is described.

Intramolecular Metal-Free C(sp3)-H Activation Enables a Selective MonoO-Debenzylation of Fully Protected Aminosugars

Carbamate-bearing benzylated aminosugars undergo an I2/I(III)-promoted intramolecular hydrogen atom transfer (IHAT) followed by a nucleophilic attack to provide polycyclic structures. Thus, suitably positioned benzyl ethers are surgically oxidized into the corresponding mixedN/O-benzylidene acetals, which can be conveniently deprotected under mild acidic conditions to grant access to selectivelyO-deprotected aminosugars amenable for further derivatization. The scope of this strategy has been proven with a series of furanosic and pyranosic scaffolds. Preliminary mechanistic studies, including Hammett LFER and KIE analyses, support a reaction pathway with nucleophilic cyclization as the rate-determining step.

Chemo-selective Rh-catalysed hydrogenation of azides into amines

Rh/Al2O3 can be used as an effective chemo-selective reductive catalyst that combines the mild conditions of catalytic hydrogenation with high selectivity for azide moieties in the presence of other hydrogenolysis labile groups such as benzyl and benzyloxycarbonyl functionalities. The practicality of this strategy is exemplified with a range of azide-containing carbohydrate and amino acid derivatives.

A new way to do an old reaction: highly efficient reduction of organic azides by sodium iodide in the presence of acidic ion exchange resin

Organic azides are readily reduced to the corresponding amines by treatment with sodium iodide in the presence of acidic ion exchange resin. The process, optimal when performed at 40 °C and 200 mbar pressure on a rotatory evaporator, is extremely efficient, clean, and tolerant of a variety of functional groups.

Synthesis and glycosidase inhibitory profiles of functionalised morpholines and oxazepanes

In this work libraries of morpholines and oxazepanes have been prepared via the reductive amination reaction between dialdehydes, derived from carbohydrates, and a range of amines. In this way, functionalised morpholines and oxazepanes have been prepared

Synthesis of new sugar-based surfactants and evaluation of their hemolytic activities

The synthesis of four sugar-based surfactants derived from glucose and (R)-12-hydroxystearic acid is described. The surfactants have a hydroxy group in the hydrophobic part, which is either free or acylated using acetyl chloride, hexanoyl chloride, or myristoyl chloride. Three of the synthesized surfactants are water-soluble and are evaluated with respect to their CMCs and hemolytic activities. The fourth surfactant has limited water solubility and is not further included in the study. The investigated surfactants are all hemolytic close to their respective CMC indicating that their use in parenteral formulations may be limited. Nevertheless, surfactants having the proposed structure appear as promising alternatives to existing solubilizing agents for pharmaceutical applications.

Efficient Synthesis of Unsymmetrical Ureido-Linked Disaccharides

Five nonsymmetrical urea-linked disaccharides, in which two glycopyranoside units are bound at the 1→2, 1→4, and 1→6 positions, were efficiently synthesized. A mild and safe procedure, in which glycosyl isocyanates were coupled with a glycosylamine, was e

Synthesis of the 2-deoxyisomaltose analogue of acarbose by an improved route to chiral valieneamines

A 2-deoxyisomaltose analogue of acarbose was stereoselectively synthesised in 11 steps with a total yield of 7% starting from 2,6-dibromo-2,6-dideoxy-D-mannono-1,4-lactone (6). The latter was reduced to the lactol, converted to the methyl glycoside (7) and hydrogenated to the 6-bromo-2,6-dideoxyglycoside (8). Benzylation of the hydroxy groups, elimination of bromine to a 5-ene and Ferrier carbocyclisation gave (2S,3R)-2,3-bisbenzyloxycyclohex-5-enone (12). 1,2-addition of benzyloxymethyl lithium at -110 C gave a 6:1 mixture of tertiary alcohols 13; the (1S) isomer was the major one. Reaction with trichloroacetyl isocyanate gave a carbamate 19, which, when dehydrated to the cyanate, spontaneously underwent [1,3] sigmatropic rearrangement to an isocyanate, which on addition of methanol gave the methylcarbamate 20. Basic hydrolysis of this compound gave (2R,3R,5R)-5-amino-1-benzyloxy-methyl-2,3-bis(benzyloxy)cyclohex-6-ene (22), which could be deprotected to 2-deoxyvalieneamine (5). Reaction with 2-azidoethyl 2,3,4-tri-O-benzyl-6-O-triflyl-α-D-glucopyranoside (34) gave the secondary amine 35, which was completely de-O-protected with sodium in ammonia to give 6-deoxy-6-((1R,3R,4R)-3,4-dihydroxy-5-hydroxymethylcyclohex-5-enylamino)-D- glucose (4), the 2-deoxyisomaltose analogue of acarbose.

Syntheses of trehazolin derivatives and evaluation as glycosidase inhibitors

The trehazolin derivatives 9-12 were synthesized from the aminocyclitol (7), which is the degradation product of trehazolin (5). In particular, compounds 9-11 were pseudodisaccharides that underwent replacement of the corresponding nonreducing D-glucose m