201043-07-4

Basic information

• Product Name: allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside
• Synonyms: allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside
• CAS NO: 201043-07-4
• Molecular Weight: 304.34
• Mol File: 201043-07-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside(201043-07-4)
• EPA Substance Registry System: allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside(201043-07-4)

Safety Data

• Hazardous Substances Data: 201043-07-4(Hazardous Substances Data)

Upstream product

• 201043-05-2 (1S,3R,4R,6R,7S,10R)-7-Allyloxy-10-hydroxy-3,4-dimethoxy-3,4-dimethyl-2,5,8-trioxabicyclo[4.4.0]decane 
• 67-56-1 methanol 

Downstream Products

• 196859-37-7 allyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranoside 
• 172795-17-4 allyl 2-O-benzyl-α-D-xylopyranoside 
• 242147-27-9 Dithiocarbonic acid O-[(2S,3S,4aR,7S,8R,8aS)-2,3-dimethoxy-2,3-dimethyl-7-(2-trityloxy-ethoxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-8-yl] ester S-methyl ester 
• 242147-26-8 2-(trityloxy)ethyl 3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-xylopyranoside 
• 242147-28-0 2-(trityloxy)ethyl-2-deoxy-3,4-O-[(2S,3S)-2,3-dimethoxybutane-2,3-diyl]-α-D-threo-pentopyranoside 
• 418766-90-2 9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine 
• 418767-00-7 9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine 
• 418766-81-1 [2-hydroxy-3-(6-amino-9H-purin-9-yl)propyl] 2-O-benzyl-3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside 
• 418766-88-8 [(2R)-[2-hydroxy-3-(6-amino-9H-purin-9-yl)]propyl] 2-O-benzyl-α-D-xylopyranoside 
• 418766-97-9 [(2S)-3-(6-amino-9H-purin-9-yl)-2-hydroxypropyl] 2-O-benzyl-α-D-xylopyranoside 
• 418766-78-6 [(2S)-2,3-epoxypropyl] 2-O-benzyl-3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside 
• 418766-76-4 [(2S)-3-azido-2-hydroxypropyl] 2-O-benzyl-α-D-xylopyranoside 
• 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 

Relevant articles and documents

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.