121964-05-4

Upstream product

• 111476-62-1 3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-D-mannitol 
• 69-65-8 mannitol 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 

Downstream Products

• 323580-65-0 Acetic acid (2R,3R,4R)-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-butyl ester 
• 106929-09-3 (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal 
• 121964-07-6 2,3-di-O-benzyl-4,5-O-isopropylidene-D-arabinitol 
• 436148-62-8 Toluene-4-sulfonic acid (2R,3S)-2,3-bis-benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propyl ester 
• 441285-23-0 (2R,3S,4R)-5-azido-3,4-bis-benzyloxy-1,2-O-isopropylidene pentane 
• 292074-24-9 (4R,5S,6R)-4,5-dibenzyloxy-7-[N-(tert-butoxycarbonyl)amino]-6-methoxymethyloxy-1-pivaloyloxy-2-heptene 
• 292074-25-0 (4R,5S,6R)-4,5-dibenzyloxy-7-[N-(tert-butoxycarbonyl)amino]-6-methoxymethyloxy-2-hepten-1-ol 
• 292074-23-8 (4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene 
• 292074-33-0 (2R,3S,4R)-3,4-dibenzyloxy-2-methoxymethyloxy-7-pivaloyloxy-5-heptenamine 

Relevant academic research and scientific papers

Inversion of regioselectivity in reactions of diols through the use of hexamethylenestannylene acetals as intermediates

Hexamethylenestannylene acetals obtained from a variety of carbohydrate-derived terminal 1,2-diols give good to excellent regioselectivity for tosylation at the secondary oxygen. In contrast, non-cyclic dialkylstannylene acetals react mainly at the primary oxygen. These results are attributed to the greater stability of the dominant stannylene acetal dimers for hexamethylenestannylene acetals.

Total synthesis of (+)-aspicilin from D-mannitol

The total synthesis of the 18-membered lichen macrolide, (+)-aspicilin, has been accomplished utilizing the Swern oxidation, Masamune-Roush olefination, and ring-closing metathesis of a trienic ester as key steps. d-Mannitol has been utilized as the chiral pool material for the construction of the olefinic aldehyde and the Jacobsen hydrolytic kinetic resolution has been employed for the construction of the olefinic phosphonate ester.

Palladium(II)-catalyzed cyclization of urethanes and its application to a total synthesis of 1-deoxynojirimycin

We have employed a palladium(II)-catalyzed cyclization of allylic alcohol as a key reaction to achieve a total synthesis of the azasugar 1-deoxynojirimycin from o-mannitol. This reaction should be useful for the stereoselective construction of natural poly-substituted piperidine derivatives.

Novel peptides comprising furanoid sugar amino acids for the treatment of cancer

Anticancer peptides which incorporate furanoid sugar amino acids and compositions made using these peptides are described. Methods for synthesis of the peptides and for preparing the furanoid sugar amino acids are disclosed. The peptides and compositions made using the peptides have pharmacological applications of these peptides especially in the treatment and prevention of cancer and tumors.

Total synthesis of (-)-microcarpalide from d-mannitol

The total synthesis of the actin-targeting metabolite (-)-microcarpalide is described. Ring-closing metathesis of a dienic ester was used as the key step. d-Mannitol was used as the chiral pool material for the construction of the olefinic acid moiety as well as the olefinic alcohol moiety of the molecule.

An efficient strategy for the synthesis of 5-hydroxyalkylbutan-4-olides from D-mannitol: Total synthesis of (-)-muricatacin

A general approach towards the synthesis of 5-hydroxyalkylbutan-4-olides from D-mannitol has been described. The approach has successfully been used for the total synthesis of (-)-muricatacin, an anti-tumor natural product.

Synthesis and structural studies of oligomers of 6-amino-2,5-anhydro-6-deoxy-D-mannonic acid

A novel cycloetherification process involving a facile 5-exo S(N)2-type ring closure by intramolecular opening of a terminal aziridine ring by a γ-hydroxyl group, led to the stereoselective synthesis of 6-amino-2,5-anhydro-6-deoxy-D-mannonic acid (1). Oligomerization of 1 by solution phase peptide coupling methods gave oligomers 2-5. While most of the oligomers, in either protected or deprotected form, did not show any significant secondary structure, octamer 5 (P = H) exhibited a very strong positive band at 216 nm in its CD spectrum in MeOH and TFE, indicating the possibility of the presence of an ordered structure in solution. Its 1H NMR spectra in various polar solvents, however, failed to produce any distinct dispersion of the amide proton chemical shifts. Compounds 1-5 were found to be inactive in hypoglyceamic tests in rats. (C) 2000 Elsevier Science Ltd.

Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin.

The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.

2,5-Anhydro sugar diacid and 2,5-anhydro sugar diamine based C2 symmetric peptidomimetics as potential HIV-1 protease inhibitors

Conformationally constrained molecular frameworks of the 2,5-anhydro sugar diacid (9) and 2,5-anhydro sugar diamines (10, 11) were used to construct architecturally beautiful novel C2 symmetric peptidomimetics 1-8. Although none of these compou

Control of regioselectivity in reactions of dialkylstannylene acetals. Part I. A dramatic reversal of regioselectivity in mono-p-toluenesulfonation reactions

The regioselectivities of p-toluenesulfonation reactions of dialkylstannylene acetals obtained from a number of carbohydrate-derived terminal 1,2-diols in the absence of added nucleophiles have been explored as functions of the carbohydrate structure, the