28161-52-6

Basic information

• Product Name: (2R,3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol
• Synonyms: beta-D-Fucose;(2R,3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol
• CAS NO: 28161-52-6
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.16
• Mol File: 28161-52-6.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 323.9°Cat760mmHg
• Flash Point: 149.7°C
• Appearance: /
• Density: 1.556g/cm³
• PKA: 12.28±0.70(Predicted)
• CAS DataBase Reference: (2R,3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol(28161-52-6)
• EPA Substance Registry System: (2R,3R,4S,5S,6R)-6-methyloxane-2,3,4,5-tetrol(28161-52-6)

Safety Data

• Hazardous Substances Data: 28161-52-6(Hazardous Substances Data)

Upstream product

• 84954-97-2 chikusaikoside I 
• 77174-32-4 Zizyphus saponin I 
• 55466-05-2 Zizyphus saponin III 
• 865688-88-6 quercitrin 
• 1207550-42-2 3-O-β-D-galactopyranosyl-(1->3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranosyl ester 
• 1207550-40-0 3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1->4)-α-L-arabinopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranosyl ester 
• 74032-91-0 p-nitrophenyl α-D-fucopyranoside 

Downstream Products

• 65310-00-1 (3S,4R,5S,6S)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 57472-03-4 methyl β-L-fucofuranoside 
• 57472-02-3 methyl α-L-fucofuranoside 
• 14687-15-1 methyl L-fucopyranoside 
• 1128-40-1 methyl β-L-fucopyranoside 
• 1128-40-1 methyl 6-deoxy-β-D-galactopyranoside 
• 1128-40-1 methyl α-D-fucopyranoside 
• 95120-27-7 6-Deoxy-β-D-allofuranosid 
• 3359-35-1 benzyl-6-deoxy-L-gulose 
• 84911-80-8 benzyl-6-deoxy-α-L-gulose 
• 84911-79-5 benzyl-6-deoxy-β-L-gulose 
• 52628-69-0 2,4-dinitrophenyl-6-deoxy-β-D-galactopyranoside 
• 196397-58-7 phenyl 3,4-O-isopropylidene-1-thio-α-L-fucopyranoside 
• 196397-59-8 phenyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 

Relevant articles and documents

Presenegenin glycosides from securidaca welwitschii

The five new presenegenin glycosides 1-5 were isolated from Securidaca welwitschii, together with one known sucrose diester. Compounds 1-4 were obtained as pairs of inseparable (E)/(Z)-isomers of a 3,4-dimethoxycinnamoyl derivative, i.e., 1/2 and 3/4. Their structures were elucidated mainly by 2D-NMR techniques and mass spectrometry as 3-O-(β-D-glucopyranosyl)presenegenin 28-{O-β-D-xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2) -O-[β-D-glucopyranosyl-(1→3)]-4-O-[(E)-3,4-dimethoxycinnamoyl] -β-D-fucopyranosyl} ester (1) and its (Z)-isomer 2, 3-O-(β-D- glucopyranosyl)presenegenin 28-{O-β-D-galactopyranosyl-(1→4)-O-β- D-xylopyranosyl-(1→4)-O-3-O-acetyl-α-L-rhamnopyranosyl-(1→2) -O-[β-D-glucopyranosyl-(1→3)]-4-O-[(E)-3,4-dimethoxycinnamoyl] -β-D-fucopyranosyl} ester (3) and its (Z)-isomer 4, and 3-O-(β-D-glucopyranosyl)presenegenin 28-[O-β-D-galactopyranosyl- (1→3)-O-β-D-xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl- (1→2)-β-D-fucopyranosyl] ester (5) (presenegenin=(2β,3β, 4α)-2,3,27-trihydroxyolean-12-ene-23,28-dioic acid). Copyright 2010 Verlag Helvetica Chimica Acta AG, Zuerich, Switzerland.

STEROIDS OF THE FUROSTAN AND SPIROSTAN SERIES FROM Nolina microcarpa II. STRUCTURES OF NOLINOSPIROSIDE D AND NOLINOFUROSIDES D, E, AND F

Proofs are given of the structures of two new glycosides of the furostan series isolated from the leaves of the plant Nolina microcarpa S.Wats. (family Dracaenaceae).Nolinofuroside D is (25S)-furost-5-ene-1β, 3β,22 α,26-tetraol 1-O-β-D-galactopyranoside 26-O-β-D-glucopyranoside (I), and nolinofuranoside F is (25S)-furost-5-ene-1β,3β,22α,26-tetraol 1-O-β-D-fucopyranoside 26-O-β-D-glucopyranoside 3-O-α-L-rhamnopyranoside (VII).The latter was characterized as its 22-O-methyl ether (VIII).Nolinofuranoside E (IV) has the structure of (25S)-furost-5-ene-1β,3β,22α,26-tetraol 26-O-β-glucopyranoside 1-O- 2)-β-D-fucopyranoside>, which followed from the structure of the fermentation product (VI).The products of the fermentation of the above-named compounds were present in the plant in only trace amounts.Only one of them - nolinospiroside D (III) - has not been described previously.This monoside of the spirostan series is (25S)-spirost-5-ene-1β,3β-diol 1-O-β-D-galactopyranoside.

Bioactive oleanane-type saponins from Hylomecon Japonica

Six undescribed oleanane-type saponins, named as Hylomeconosides L-Q, were isolated from the whole herb of Hylomecon Japonica, their structures were determined by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HRESI-MS) and chromatographic data (GC and LC). Their structures were identified as 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranoside. Hylomeconosides L-Q showed selective cytotoxicities against human cancer cell lines A549, AGS, HeLa, Huh 7, HT29 and K562. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon Japonica and their bioactivities.

Triterpene saponins from Silene gallica collected in North-Eastern Algeria

Eleven previously undescribed triterpene saponins, named silenegallisaponin A-K (1–11), were isolated from the aerial parts of Silene gallica L. Their structures were elucidated by analysis of 1D and 2D-NMR spectroscopic data and mass spectrometry (HR-ESI-MS). The saponins comprised caulophyllogenin, echinocystic acid, or quillaic acid substituted at C-3 by a β-D-glucuronic acid or β-D-galactopyranosyl-(1 → 3)-β-D-glucuronopyranoside and at C-28 by a β-D-fucopyranose substituted at C-2 by a β-D-glucose and at C-3 by a β-D-glucose or a β-D-quinovose.