Просмотр кода страницы Английская Википедия:1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose

{{Английская Википедия/Панель перехода}}
{{DISPLAYTITLE:1-''O''-Acetyl-2,3,5-tri-''O''-benzoyl-beta-<small>D</small>-ribofuranose}}
{{Chembox
|ImageFile = 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose.png
|IUPACName = β-<small>D</small>-Ribofuranose 1-acetate 2,3,5-tribenzoate
|SystematicName = (2''S'',3''R'',4''R'',5''R'')-2-(Acetyloxy)-5-[(benzoyloxy)methyl]oxolane-3,4-diyl dibenzoate
|Section1={{Chembox Identifiers
| CASNo = 6974-32-9
| ChemSpiderID = 73498
| EC_number = 230-220-4
| PubChem = 81455
| StdInChI=1S/C28H24O9/c1-18(29)34-28-24(37-27(32)21-15-9-4-10-16-21)23(36-26(31)20-13-7-3-8-14-20)22(35-28)17-33-25(30)19-11-5-2-6-12-19/h2-16,22-24,28H,17H2,1H3/t22-,23-,24-,28-/m1/s1
| StdInChIKey = GCZABPLTDYVJMP-CBUXHAPBSA-N
| SMILES = CC(=O)O[C@H]1[C@@H]([C@@H]([C@H](O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
 }}
|Section2={{Chembox Properties
|C=28|H=24|O=9
 }}
}}
'''1-''O''-Acetyl-2,3,5-tri-''O''-benzoyl-beta-<small>D</small>-ribofuranose''', also called '''β-<small>D</small>-ribofuranose 1-acetate 2,3,5-tribenzoate''', is a [[ribose]]-derived compound used in [[Synthesis of nucleosides|nucleoside synthesis]].<ref>{{Cite journal|last1=Niedballa|first1=U.|last2=Vorbrueggen|first2=H.|date=1976-06-01|title=Synthesis of nucleosides 17. A general synthesis of ''N''-glycosides. 6. On the mechanism of the stannic chloride catalyzed silyl Hilbert–Johnson reaction|url=https://doi.org/10.1021/jo00874a002|journal=The Journal of Organic Chemistry|volume=41|issue=12|pages=2084–2086|doi=10.1021/jo00874a002|pmid=932850|issn=0022-3263}}</ref>

== Industrial synthesis ==
In the patented formation of 1-''O''-acetyl-2,3,5-tri-''O''-benzoyl-beta-<small>L</small>-ribofuranose, a reactor containing [[thionyl chloride]] (5&nbsp;ml) and [[methyl alcohol]] (100 ml) is stirred at 0–5&nbsp;°C for 10 to 15 minutes. After this period, 10&nbsp;g (ratio-wise) of [[ribose]] is added to the flask. The flask is then stirred and maintained at its temperature for 8 hours. During this period, a [[methylation]] reaction will occur on the ribose. After the 8-hour period of methylation, the flask will be filled with 150&nbsp;ml of [[ethyl acetate]], 5&nbsp;ml [[pyridine]], and 30&nbsp;g [[potassium carbonate]]. The flask will then be heated to 60–70&nbsp;°C. Over 99 minutes at this temperature, 30&nbsp;ml of the chemical [[benzyl chloride]] will be intermittently dripped into the flask to react with the ribose directly. After this period, the flask will be left for 4 to 8 hours to continue reacting. The subsequent solid nonacetylated ribose benzyl glycoside will be isolated by neutralizing the flask liquid by addition of [[sulfuric acid]], then suction of the precipitate (the non-acetylated ribose benzyl glycoside). The benzyl ribose glucoside will then be put into a separate flask. In this flask, [[glacial acetic acid]] and [[acetic anhydride]] will be mixed with the benzyl glycoside under a maintained temperature from −5 to 5&nbsp;°C for 5 hours. The 1-''O''-acetyl-2,3,5-tri-''O''-benzoyl-beta-<small>L</small>-ribofuranose will be the product yielded after recrystallization with [[ethyl alcohol]] and isolation by known filtering methods.<ref>{{Cite patent|country=CN|number=102659856|title=Preparation technology of 1-''O''-acetyl-2,3,5-tri-''O''-benzoyl-beta-<small>D</small>-ribofuranose|gdate=2012-04-10|pubdate=2012-09-12|assign=Changzhou Kangli Pharmaceutical Co. Ltd.|inventor1-first=Chen|inventor1-last=Ao|inventor2-first=Li|inventor2-last=Minghai|inventor3-first=Chen|inventor3-last=Zhengyi|inventor4-first=Jun|inventor4-last=Yu}}</ref>

== Use in artificial nucleotide synthesis ==
1-''O''-Acetyl-2,3,5-tri-''O''-benzoyl-beta-<small>D</small>-ribofuranose is further reacted with [[Trimethylsilyl trifluoromethanesulfonate]] (TMSOTf) under the ''[[Synthesis of nucleosides|silyl-Hilbert–Johnson]]'' reaction and deprotected by an acid or base to form a pure artificial nucleotide.

==References==
{{reflist}}

{{DEFAULTSORT:Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose, 1-O-}}
[[Category:Ribosides]]
[[Category:Benzoate esters]]


{{organic-compound-stub}}
{{Навигационная таблица/Портал/Английская Википедия}}
[[Категория:Английская Википедия]]
[[Категория:Википедия]]
[[Категория:Статья из Википедии]]
[[Категория:Статья из Английской Википедии]]