Synthesis of Methyl-3,4-Dideoxy-α(β)-D-glycero-hex-3-enopyranosiduloses from Levoglucosenone
Publication type: Journal Article
Publication date: 2021-07-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Opening of the 1,6-anhydro bridge in levoglucosenone by the action of acetic anhydride in the presence of ZnCl2 afforded diastereoisomeric 1,6-di-O-acetyl-3,4-dideoxy-α/β-D-glycero-hex-3-enopyranos-2-uloses, and alcoholysis of the resulting diacetates in methanol, ethanol, and propan-2-ol in the presence of p-toluenesulfonic acid, camphor-10-sulfonic acid, ZnCl2, and HCl was studied. Their methanolysis in the presence of CSA gave methyl 3,4-dideoxy-α/β-D-glycero-hex-3-enopyranosid-2-uloses that are precursors to purpurosamine C and (+)-frontalin.
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Russian Journal of Organic Chemistry
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Faizullina L. Kh. et al. Synthesis of Methyl-3,4-Dideoxy-α(β)-D-glycero-hex-3-enopyranosiduloses from Levoglucosenone // Russian Journal of Organic Chemistry. 2021. Vol. 57. No. 7. pp. 1047-1052.
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Faizullina L. Kh., Galimova Yu. S., Khalilova Yu. A., Valeev F. A. Synthesis of Methyl-3,4-Dideoxy-α(β)-D-glycero-hex-3-enopyranosiduloses from Levoglucosenone // Russian Journal of Organic Chemistry. 2021. Vol. 57. No. 7. pp. 1047-1052.
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TY - JOUR
DO - 10.1134/s1070428021070034
UR - https://doi.org/10.1134/s1070428021070034
TI - Synthesis of Methyl-3,4-Dideoxy-α(β)-D-glycero-hex-3-enopyranosiduloses from Levoglucosenone
T2 - Russian Journal of Organic Chemistry
AU - Faizullina, L Kh
AU - Galimova, Yu S
AU - Khalilova, Yu A
AU - Valeev, F A
PY - 2021
DA - 2021/07/01
PB - Pleiades Publishing
SP - 1047-1052
IS - 7
VL - 57
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2021_Faizullina,
author = {L Kh Faizullina and Yu S Galimova and Yu A Khalilova and F A Valeev},
title = {Synthesis of Methyl-3,4-Dideoxy-α(β)-D-glycero-hex-3-enopyranosiduloses from Levoglucosenone},
journal = {Russian Journal of Organic Chemistry},
year = {2021},
volume = {57},
publisher = {Pleiades Publishing},
month = {jul},
url = {https://doi.org/10.1134/s1070428021070034},
number = {7},
pages = {1047--1052},
doi = {10.1134/s1070428021070034}
}
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MLA
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Faizullina, L. Kh., et al. “Synthesis of Methyl-3,4-Dideoxy-α(β)-D-glycero-hex-3-enopyranosiduloses from Levoglucosenone.” Russian Journal of Organic Chemistry, vol. 57, no. 7, Jul. 2021, pp. 1047-1052. https://doi.org/10.1134/s1070428021070034.