923133
左旋葡萄糖酮
≥95%
别名:
(1S,5R)-6,8-二氧杂双环[3.2.1]辛-2-烯-4-酮, 1,6-脱水-3,4-双脱氧十六烷-3-烯吡喃-2-酮糖, 6,8-二氧杂双环[3.2.1]辛-2-烯-4-酮
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关于此项目
经验公式（希尔记法）:
C6H6O3
化学文摘社编号:
分子量:
126.11
UNSPSC Code:
12352201
NACRES:
NA.22
MDL number:
InChI
1S/C6H6O3/c7-5-2-1-4-3-8-6(5)9-4/h1-2,4,6H,3H2/t4-,6+/m0/s1
SMILES string
[H][C@]1(C=CC2=O)CO[C@]2([H])O1
InChI key
HITOXZPZGPXYHY-UJURSFKZSA-N
assay
≥95%
form
liquid
greener alternative product characteristics
Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.
sustainability
Greener Alternative Product
refractive index
n/D 1.50625
density
1.32 g/mL
functional group
ether, ketone
greener alternative category
, Aligned
storage temp.
2-8°C
Quality Level
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相关类别
General description
We are committed to bringing you greener alternative products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product is biorenewable and thus aligns with ″Safer Solvents and Auxiliaries″ and ″Use of Renewable Feedstocks″. Click here for more information.
Levoglucosenone undergoes Michael-addition reaction with diethyl malonate, ethyl cyanoacetate, 2-nitropropane and 2-methylcyclohexanone in the presence of various catalysts to afford 4-substituted levoglucosenone derivatives having the D-erythro configuration.
Levoglucosenone undergoes Michael-addition reaction with diethyl malonate, ethyl cyanoacetate, 2-nitropropane and 2-methylcyclohexanone in the presence of various catalysts to afford 4-substituted levoglucosenone derivatives having the D-erythro configuration.
Application
Levoglucosenone may be used in the synthesis of the following:
- Various deoxy, keto and branched-chain sugars
- 4-thio and 4-substituted sugar derivatives
- Natural stereoisomer of serricornin
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2
存储类别
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Recent Applications of Levoglucosenone as Chiral Synthon.
Sarotti A M, et al.
Current Organic Synthesis, 9(4), 439-459 (2012)
Levoglucosenone and Its New Applications: Valorization of Cellulose Residues.
Comba M B, et al.
European Journal of Organic Chemistry, 590-604 (2018)
Jonas Kühlborn et al.
Natural product reports, 37(3), 380-424 (2019-10-19)
Covering: up to mid-2019 This review highlights the utilization of biomass-derived building blocks in the total synthesis of natural products. An overview over several renewable feedstock classes, namely wood/lignin, cellulose, chitin and chitosan, fats and oils, as well as terpenes
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