136738-66-4

Upstream product

• 492-61-5 β-D-glucose 
• 25152-90-3 (4aR,6S,7R,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol 
• 81846-60-8 nitromethyl β-D-glucopyranoside 
• 144-55-8 sodium hydrogencarbonate 
• 501-53-1 benzyl chloroformate 
• 136738-59-5 2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-guloheptitol 
• 136738-62-0 1-amino-2,6-anhydro-5,7-O-benzylidene-1-deoxy-D-glycero-D-guloheptitol 
• 2280-44-6 D-Glucose 
• 136738-65-3 2,6-anhydro-5,7-O-benzylidene-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol 

Downstream Products

• 169597-64-2 (2S,3S,4R,5R,6S)-6-(Benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid 
• 156058-64-9 (2S,3S,4R,5R,6S)-6-(Benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Use of D-glucopyranuronic acids and their derivatives for incorporation in pharmacologically active peptides and their salts

Use of 7-amino-L-glycero-L-gulo-2,6-anhydro-7-desoxy-heptonic acid and 2-benzoxycarbonylamino-01 -methyl-2-desoxy-β-glucopyranuronic acid, their derivatives and the enantiomorphous compounds for incorporation and for manufacture in pharmacologi

C-glycoside synthesis II: Henkt condensations of 4,6-O-alkylidene pyranoses with a 1,3-proton transfer catalyst- a roote to blocked aminomethyl-c-glycosides

In the presence of a novel 1,3-proton transfer catalyst (2-hydroxypyridine (2-HP)/ 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)/molecular sieves), 4,6-Obenzylidene-D-glucopyranose (1),4,6-O-isopropylidene-D-mannose (12), and 4,6-O-isopropyridene-D-glucose (16) undergo Henry condensations with nitromethane in THF to give acetal protected nitromethyl C-glycopyranosides (2, 13, and 17, respectively), which were characterized as their O-acetyl derivatives (5, 15, and 18, respectively). The Henry product from 4,6-O-benzyridene-D glucopyranose could be reduced, with retention of the 4,6-O-benzylidene protecting group, by a specially prepared form of elemental iron in aqueous tetrahydrofuran under CO2 to aminomethyl-C-glycopyranoside (16), characterized as N-acetyl, peracetyl, and N-Cbz derivatives (7, 8, 9, 10), and converted with diazonium salt to a triazene derivative (II). Nitroalkenes are only mechanistic intermediates in our condensations with nitromethane, but they undergo Michael additions with a second mole of nitromethane to give novel 5,7-O-alkylidene-1,2-deoxy-1 nitro-2-nitromethyl-D-heptitols (3 and 14) as side-products.