140156-32-7

Upstream product

• 3969-61-7 2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol 
• 100-39-0 benzyl bromide 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 

Downstream Products

• 81801-08-3 4-O-benzyl-2,3-O-isopropylidene-aldehydo-D-erythrose 
• 287119-12-4 (3E)-7-O-benzyl-2-O-[(tert-butyl)dimethylsilyl]-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-1,3-dienitol 
• 287119-11-3 (3E)-7-O-benzyl-1,3,4-trideoxy-5,6-O-isopropylidene-D-erythro-hept-3-en-2-ulose 
• 157968-84-8 1-O-benzyl-4-O-(1-ethoxycarbonylethyl)-2,3:5,6-di-O-isopropylidene-D-mannitol 
• 140156-29-2 1-O-benzyl-4-O-ethoxycarbonylmethyl-2,3:5,6-di-O-isopropylidene-D-mannitol 

Relevant academic research and scientific papers

A practical approach to regioselective O-benzylation of primary positions of polyols

Exposure of saccharide polyols to a moderate excess of benzyl bromide and DIPEA at 90 °C results in the regioselective O-benzylation of primary positions in moderate to good yields. The reactions can be performed without inert atmosphere and provide synth

Enantioselective synthesis of ethyl 4,5,7,8,9-penta-O-acetyl-2,6- anhydro-3-deoxy-D-erythro-L-gluca-nononate: A 2-monodeoxygenated derivative of '2-keto-3-deoxy-D-glycero-D-galacto-nononic acid'

A study aimed at developing an enantioselective synthesis of the title compound 23, a 2-monodeoxy analogue of the naturally occurring (+)-2-keto-3- deoxy-D-glycero-D-galacto-2-nononic acid (KDN), is reported. From D-mannose as starting material, the chiral 1,3-diene 10, activated by a silyloxy substituent at C(2), was prepared in six steps (Scheme 1). However, the intermediates were often contaminated with varying amounts of by-products arising from overoxidation during cleavage with periodic acid. An alternative route starting from the inexpensive and readily available D-isoascorbic acid (12), though a little longer than the first, satisfactorily circumvented the purification problem and led to the desired dienes 17 in good yields (scheme 2). The [Co11(S,S)-(+)-salen]-catalyzed hetero-Diels-Alder reactions of the aforementioned dienes with ethyl glyoxylate proceeded smoothly at room temperature, giving the dihydropyrano adducts 18 in moderate yields (Scheme 3). Dihydroxylation of 18a followed by reduction of the keto function gave the desired 4,5-trans dihydroxy moiety of the KDN framework (Scheme 4, see 21). The spectroscopic data of the penta-O-acetylated 2-deoxy-KDN ethyl ester 23 were consistent with those reported for the corresponding methyl ester derived from natural KDN.

A new synthesis of 2-deoxy-β-Kdo, a potent CMP-Kdo synthetase inhibitor

In this paper, the authors describe a new, stereospecific synthesis of 2-deoxy-beta-Kdo which also starts from D-mannose.