54497-89-1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 

Downstream Products

• 19186-53-9 methyl-[tetrakis-O-(toluene-4-sulfonyl)-β-D-glucopyranoside] 
• 96530-38-0 methyl 6-deoxy-6-iodo-2-O-p-toluenesulfonyl-α-D-glucopyranoside 
• 136471-95-9 methyl 3,4-bis(O-methoxymethyl)-2,6-bis-α-D-glucopyranoside 
• 96711-93-2 methyl 3,4-di-O-benzoyl-2,6-di-O-tosyl-α-D-glucopyranoside 
• 165375-09-7 methyl 3-O-benzoyl-2,6-di-O-tosyl-α-D-glucopyranoside 
• 96691-87-1 methyl 4-O-benzoyl-3-O-benzyl-6-deoxy-6-iodo-2-O-(p-tolylsulphonyl)-α-D-gulopyranoside 
• 96691-88-2 methyl 3,4-di-O-benzyl-6-deoxy-6-iodo-2-O-(p-tolylsulphonyl)-α-D-gulopyranoside 
• 96691-89-3 Toluene-4-sulfonic acid (E)-(S)-1-((1R,2S)-1,2-bis-benzyloxy-but-3-enyl)-4-oxo-pent-2-enyl ester 
• 96691-86-0 methyl 3-O-benzyl-6-deoxy-6-iodo-2-O-(p-tolylsulphonyl)-α-D-gulopyranoside 
• 96691-85-9 methyl 3,4-anhydro-6-deoxy-6-iodo-2-O-(p-tolylsulphonyl)-α-D-galactopyranoside 
• 165375-10-0 methyl 4-O-acetyl-3-O-benzoyl-2,6-di-O-tosyl-α-D-glucopyranoside 
• 165375-11-1 methyl 4-O-acetyl-3-O-benzoyl-6-deoxy-6-iodo-2-O-tosyl-α-D-glucopyranoside 
• 165375-14-4 (1R,5R)-6-exo-acetoxy-7-endo-benzoyloxy-N-methyl-8-exo-(toluene-p-sulfonyloxy)-3-oxa-2-azabicyclo<3.3.0>octane 
• 165375-24-6 Benzoic acid (1S,2R,3R,4S,5S)-3-acetoxymethyl-2,5-dihydroxy-4-(toluene-4-sulfonylamino)-cyclopentyl ester 

Relevant academic research and scientific papers

One-pot p-toluenesulfonylation of adenosine and methyl glycosides with a substoichiometric amount of organotin mediators

A substoichiometric amount (10-20 mol%) of dibutyltin dichloride 1 was found to be effective for promoting the regioselective 2′-O-tosylation of adenosine 2 with TsCl in a one-pot manner, wherein a turnover step for tin dichloride 1 was involved. Dibutylc

Synthesis of Methyl 6-Deoxy-6-diphenylphosphino-α-D-glucopyranoside: Temperature-Dependence of the Primary O-Tosyl Cleavage Mode

Methyl α-D-glucopyranoside is converted to methyl 6-p-toluenesulfonyl-2,3,4-tris-O-trimethylsilyl-α-D-glucopyranoside 2 and then reacted with lithium diphenylphosphide in THF. When the reaction is carried out at room temperature and below, S-O cleavage dominates giving methyl 2,3,4-tris-O-trimethylsilyl-α-D-glucopyranoside 3, whereas at 60°C in THF or at 35°C in diethyl ether, C-O cleavage occurs yielding the title carbohydrate-phosphine 4 in good yield after deprotection.

Synthesis of a 2-aminohexahydrobenzoxazole analogue related to trehazolin

2-Aminohexahydrobenzoxazole analogue 1a, related to trehazolin (2) was synthesized using the Ferrier reaction as a key step. The structural elucidation of this compound by NMR analysis indicated that it is an inseparable mixture of three components (1a-c) which in turn stems from the propensity of la to partially undergo both transcyclization (1a → 1b) of the aminooxazoline between the hydroxy group at the C-1 position of aminocyclitol in the aglycon moiety and the hydroxy group at the C-2 position of D-glucose moiety and successive transformation (1b → 1c) of the D-glucose moiety from a pyranose to a furanose structure.

Syntheses of Optically Active 2,3,6-Tri-O-benzyl-D-myo-inositol, Laminitol, and Mytilitol from D-Glucose

2,3,6-Tri-O-benzyl-D-myo-inositol, which is a key intermediate of D-inositol 1,4,5-triphosphate, was synthesized from D-glucose without performing any optical resolution by utilizing C2 symmetry.Laminitol and mytilitol were also synthesized from D-glucose

REGIOSELECTIVE STANNYLATION. ACYLATION OF CARBOHYDRATES: COORDINATION CONTROL

An efficient method for the regioselective enhancement of the nucleophilicity of polyhydroxy compounds has been developed.Partial stannylation of carbohydrate with (Bu3Sn)2O and subsequent electrophilic attack with benzoyl chloride gave rise to regioselec