29747-91-9

Usage

Class

Furanoses

Derivative

L-idose, a rare sugar and important intermediate in the synthesis of various bioactive compounds

Use

Protecting group for the hydroxyl group of sugar to prevent unwanted reactions during chemical synthesis

Applications

Synthesis of complex carbohydrates and glycosides, development of pharmaceuticals and agrochemicals

Molecular weight

190.19 g/mol

Synthesis

Typically obtained through chemical synthesis

Upstream product

• 19684-32-3 1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose 
• 7284-07-3 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-eno-furanose 
• 4118-60-9 5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose 
• 38166-60-8 1,2:5,6-di-O-isopropylidene-α-L-glucofuranoside 
• 1990-29-0 D-altrose 
• 67-64-1 acetone 
• 329899-64-1 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 

Downstream Products

• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 81562-09-6 6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside 
• 5934-56-5 glucose 
• 60619-47-8 1,6-anhydro-β-L-idopyranose 
• 5206-40-6 5-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone 
• 20513-98-8 1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone 
• 848345-34-6 (1S,4S,5R,6S,7R)-6,7-dibenzyloxy-5-nitro-2-oxabicyclo-[2.2.1]heptan-3-one 
• 848345-33-5 3,5-di-O-benzyl-6-deoxy-6-nitro-β-L-idono-1,4-lactone 
• 848345-36-8 methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-L-idofuranoside 
• 848345-31-3 3,5-di-O-benzyl-6-deoxy-6-iodo-1,2-O-isopropylidene-β-L-idofuranose 
• 848345-29-9 3,5-di-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 848345-32-4 3,5-di-O-benzyl-6-deoxy-6-nitro-1,2-O-isopropylidene-β-L-idofuranose 
• 848345-30-2 3,5-di-O-benzyl-6-O-p-toluenesulfonyl-1,2-O-isopropylidene-β-L-idofuranose 
• 848345-28-8 3,5-di-O-benzyl-6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose 

Relevant academic research and scientific papers

Synthesis from d-altrose of (5 R,6 R,7 R,8 S)-5,7-dihydroxy-8- hydroxymethylconidine and 2,4-dideoxy-2,4-imino-d-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-d-mannitol

Ring closure of a 3,5-di-O-triflate derived from d-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine.

Useful methods for the synthesis of isopropylidenes and their chemoselective cleavage

A catalytic amount of phosphotungstic acid (PTA) has been found to be a very effective catalyst for isopropylidenation of 1,2-diols and their deprotection at room temperature. The ease of handling, cost and activity of the catalyst, good to excellent yields and chemoselectivity for deprotection are some of the highlights of the reported method.

The role of the C-3 substituent in the asymmetric dihydroxylation of hexo-5-enofuranosides

Asymmetric dihydroxylation of vinyl furanosides 1-6 by use of OsO4, AD-mix-α and β is described yielding the corresponding hexofuranose sugars. Vinyl furanosides 2 and 3, with an ester group at C-3, and vinyl manno furanoside 5 on asymmetric dihydroxylation with AD-mix α exhibited high R diastereoselectivity at C-5. Reversal in diastereoselectivity at C-5 was observed for the 3-deoxy vinyl furanoside 6 giving furanosaccharide 6S with the S configuration at C-5.

ON THE STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATIONS OF ALLYLIC SYSTEMS USED IN THE SYNTHESIS OF HIGHER-CARBON SUGARS

The stereochemistry of the major osmylation products of carbohydrate-based allylic alcohols can usually be predicted by application of Kishi's empirical rule.In particular, the addition of OsO4 can be formulated as taking place in the more abundant conformation on the surface anti to a pyranose or furanose ring-oxygen atom located at a stereocentre adjacent to the olefinic linkage.Exceptions to Kishi's empirical rule for osmylation are sometimes encountered with conjugated carbonyl compounds.

PRACTICAL SYNTHESIS OF NOJIRIMYCIN

The short step and efficient synthesis of nojirimycin (1) from commercially available 1,2-isopropylidene-D-glucofuranose (2) was described.Oxidation of 2 with (Bu3Sn)2O-Br2 followed by oximation, isomerization, and stereoselective reduction gave the 5-amino derivative of gluco-configuration (6a), which was converted to nojirimycin bisulfite adduct (8) in 50percent overall isolated yield.

SYNTHESES OF 1-(5-DEOXY-Β-D-arabino-HEXOFURANOSYL)CYTOSINE

1-(5-Deoxy-β-D-arabino-hexofuranosyl)cytosine (4'-homoara-C) (11), a higher homolog of the antileukemic agent ara-C(1-β-D-arabinofuranosylcytosine), was prepared by two independent routes.The first one involved the inversion of configuration at C-2' of the D-ribo epimer (1-(5-deoxy-β-D-ribo-hexofuranosyl)cytosine, 4'-homocytidine) by the diphenylcarbonate technique; the 5-deoxy-D-ribo-hexofuranosyl moiety of 4'-homocytidine was obtained by way of an anti-Markovnikov addition of iodine trifluoroacetate to the double bond of 5,6-dideoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hex-5-enofuranose and reduction of the resulting iodide(s).In the second approach, 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-β-D-xylo-hexofuranose was acetolyzed and condensed with 4-acetyl-N-bis(trimethylsilyl)cytosine, and alkaline treatment gave 11 by way of a 2',3'-anhydro intermediate.The structure of 11, in particular the configuration at C-2', was confirmed by its 1H- and 13C-n.m.r. spectra.