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Chemical Structure| 142654-29-3 Chemical Structure| 142654-29-3

Structure of 142654-29-3

Chemical Structure| 142654-29-3

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Product Details of [ 142654-29-3 ]

CAS No. :142654-29-3
Formula : C10H19NO5
M.W : 233.26
SMILES Code : O=C(OC(C)(C)C)N(C(OC(C)(C)C)=O)O
MDL No. :MFCD24465969
Boiling Point : No data available
InChI Key :BUQTYVUSGLJSKS-UHFFFAOYSA-N
Pubchem ID :21700045

Safety of [ 142654-29-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 142654-29-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 142654-29-3 ]

[ 142654-29-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 52079-23-9 ]
  • [ 142654-29-3 ]
  • [ 666706-29-2 ]
YieldReaction ConditionsOperation in experiment
77% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0℃; for 2h; A solution of N,N-diBoc-hydroxylamine (8.5 g, 36 mmol) in dry THF (50 mL) under N2 was added Ph3P (11 g, 42 mmol) and cooled to 0C. A solution of (S)-alpha-hydroxy-gamma-butyrolactone (3.6 g, 35 mmol) in dry THF (10 mL) was added, followed by addition of DEAD (6.8 ml, 42 mmol) during 30 minutes. The dark reaction mixture was stirred at 0C until TLC (EtOAc:PE60/80 = 1:2, KMn04 spray) indicated complete conversion of (S)-alpha-hydroxy-gamma-butyrolactone (approx. 2 hours). The reaction mixture was evaporated to dryness, dissolved in ET20 (50 mL) and triturated by addition of PE40/60 (100 mL). The reaction mixture was filtered, and the precipitate thoroughly washed with Et2O:PE40/60 = 1:1 (100 mL). The combined organic filtrates were evaporated to dryness to give 16 g of brown oil. The oil was subjected to column chromatography (1000 ml SiO2, 7 cm in diameter, eluent : EtOAc:PE60/80 = 1:2). The pure fractions were combined, evaporated to dryness and washed with PE40/60 (15 mL) to give 8.5 g (77%) of enantiopure[(R)-alpha-NN-diBoc-aminoxy-gamma-butyrolactone. (R) -isomer: [alpha] D;25= +62.5 ; [alpha]365;25= +210. The (R)-isomer was prepared similarly : [alpha]D;25=-62.8 ; [alpha]365;25= -211.
 

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