196859-37-7

Basic information

• Product Name: allyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranoside
• Synonyms: allyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranoside
• CAS NO: 196859-37-7
• Molecular Weight: 520.623
• Mol File: 196859-37-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: allyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranoside(196859-37-7)
• EPA Substance Registry System: allyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranoside(196859-37-7)

Safety Data

• Hazardous Substances Data: 196859-37-7(Hazardous Substances Data)

Upstream product

• 87-72-9 D-Xylose 
• 201043-15-4 (1R,3S,4S,6R,9S,10R)-9-Allyloxy-10-benzyloxy-3,4-dimethoxy-3,4-dimethyl-2,5,8-trioxabicyclo[4.4.0]decane 
• 201043-07-4 allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside 
• 100-39-0 benzyl bromide 
• 352285-95-1 allyl 3,4-O-isopropylidene-α-D-xylopyranoside 
• 196859-36-6 allyl 2-O-benzyl-3,4-di-O-isopropylidene-α-D-xylopyranoside 
• 140420-69-5 allyl α-D-xylopyranoside 
• 2746-25-0 p-Methoxybenzyl bromide 
• 172795-17-4 allyl 2-O-benzyl-α-D-xylopyranoside 
• 824-94-2 p-methoxybenzyl chloride 
• 352285-94-0 allyl 3,4-O-isopropylidene-2-O-trimethylacetyl-α-D-xylopyranoside 
• 352285-93-9 allyl 2-O-trimethylacetyl-α-D-xylopyranoside 

Downstream Products

• 352286-05-6 1-O-[(3'R,4'S)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-β-D-xylopyranoside 3,4,3'-tris(dibenzylphosphate) 
• 352286-03-4 1-O-[(3'S,4'R)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-β-D-xylopyranoside 3,4,3'-tris(dibenzylphosphate) 
• 352286-04-5 1-O-[(3'R,4'S)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-α-D-xylopyranoside 3,4,3'-tris(dibenzylphosphate) 
• 352286-02-3 1-O-[(3'S,4'R)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-α-D-xylopyranoside 3,4,3'-tris(dibenzylphosphate) 
• 352286-01-2 1-O-[(3'R,4SR)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-β-D-xylopyranose 
• 352285-99-5 1-O-[(3'S,4'R)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-β-D-xylopyranose 
• 352286-00-1 1-O-[(3'R,4SR)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-α-D-xylopyranose 
• 352285-98-4 1-O-[(3'S,4'R)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-α-D-xylopyranose 
• 290811-02-8 2-O-benzyl-3,4-di-O-p-methoxybenzyl-D-α/β-xylopyranosyl dimethyl phosphite 

Relevant articles and documents

Xylopyranoside-based agonists of D-myo-inositol 1,4,5-trisphosphate receptors: Synthesis and effect of stereochemistry on biological activity

The synthesis of a series of tetrahydrofuranyl α- and β-xylopyranoside trisphosphates, designed by excision of three motifs of adenophostin A is reported. The synthetic route features improved preparations of allyl α-D-xylopyranoside and its 2-O-benzyl ether, and gives access to four diastereoisomeric trisphosphates, which show a range of abilities to mobilise Ca2+ from the intracellular stores of hepatocytes. A comparison of the potencies of the four trisphosphates provides useful information relating to the effects of stereochemical variation on the recognition of carbohydrate-based trisphosphates by D-myo-inositol 1,4,5-trisphosphate receptors. 1-O-[(3′S,4′R)-3-hydroxytetrahydrofuran-4-yl] α-D-xylopyranoside 3,4,3′-trisphosphate (8) is the most active member of the series with a potency close to Ins(1,4,5)P3; a β-linked analogue, 1-O-[(3′R,4′S)-3-hydroxytetrahydrofuran-4-yl] β-D-xylopyranoside 3,4,3′-trisphosphate, is ca. 20-fold weaker than Ins(1,4,5)P3, and the other compounds are much less active. While no compound attained a potency close to that of adenophostin A, we believe that 8 represents the minimal structure for potent Ca2+-releasing activity in this type of carbohydrate-based analogue.

Total synthesis, from D-xylose, of chiral, ring-contracted 1D-myo-inositol 1,4,5-trisphosphate and 1,3,4,5-tetrakisphosphate analogues with C-2 excised

A route to chiral, cyclopentane-based congeners of the second messenger 1D-myo-inositol 1,4,5-trisphosphate and its enigmatic metabolite 1D-myo-inositol 1,3,4,5-tetrakisphosphate, starting from D-xylose, is described.Reaction of allyl α-D-xylopyranoside 7 with 2,2,3,3-tetramethoxybutane gave a 1:1 mixture of the 2,3- and 3,4-butanediacetal-protected derivatives 8 and 9.The latter was converted in four steps into 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-D-xylopyranose 15, which on reduction with sodium borohydride gave 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-D-xylitol 16.Swern oxidation followed by samarium(II) iodide-mediated pinacol coupling gave a 1:3 mixture of 1L-1,2,3,4/5-1-benzyloxy-2,3-dihydroxy-4,5-bis-(p-methoxybenzyloxy)cyclopentane 18 and 1L-1,2,4/3,5-3-benzyloxy-1,2-dihydroxy-4,5-bis-(p-methoxybenzyloxy)cyclopentane 19.The identity of the latter was confirmed by conversion into known compounds, and further elaboration gave the target compounds, 1D-1,2,4/3,5-cyclopentanepentaol 1,3,4-trisphosphate 5 and 1D-1,2,4/3,5-cyclopentanepentaol-1,2,3,4-tetrakisphosphate 6.