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[ CAS No. 3519-30-0 ] {[proInfo.proName]}

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Chemical Structure| 3519-30-0
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Product Details of [ 3519-30-0 ]

CAS No. :3519-30-0 MDL No. :MFCD04972376
Formula : C9H18O3 Boiling Point : -
Linear Structure Formula :- InChI Key :XQTIFSCLEWPKCF-ZETCQYMHSA-N
M.W : 174.24 Pubchem ID :12943847
Synonyms :

Safety of [ 3519-30-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3519-30-0 ]

* 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 [ 3519-30-0 ]

[ 3519-30-0 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 42417-65-2 ]
  • [ 3519-30-0 ]
  • [ 18668-10-5 ]
  • 2
  • [ 1149-26-4 ]
  • [ 3519-30-0 ]
  • [ 13516-17-1 ]
YieldReaction ConditionsOperation in experiment
99% With dmap; dicyclohexyl-carbodiimide In dichloromethane for 24h; Ambient temperature;
(i) PhSO2Cl, Py, (ii) /BRN= 4658890/; Multistep reaction;
  • 3
  • [ 53978-73-7 ]
  • [ 3519-30-0 ]
  • [ 18668-09-2 ]
  • 4
  • [ 61083-59-8 ]
  • [ 3519-30-0 ]
  • [ 82301-82-4 ]
YieldReaction ConditionsOperation in experiment
92% With pyridine In dichloromethane at 0℃; for 4h;
  • 5
  • [ 82301-82-4 ]
  • [ 3519-30-0 ]
YieldReaction ConditionsOperation in experiment
75% With dimethyl amine In methanol at 0℃; for 0.5h;
  • 6
  • [ 2448-45-5 ]
  • [ 3519-30-0 ]
  • [ 174743-59-0 ]
YieldReaction ConditionsOperation in experiment
84% With dmap; dicyclohexyl-carbodiimide In dichloromethane for 20h;
  • 7
  • [ 524-38-9 ]
  • [ 3519-30-0 ]
  • [ 380886-38-4 ]
YieldReaction ConditionsOperation in experiment
75% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran
  • 8
  • [ 380886-48-6 ]
  • [ 3519-30-0 ]
YieldReaction ConditionsOperation in experiment
73% With water; potassium carbonate In methanol at 0℃; for 2h; tert-Butyl (S)-2-hydroxy-3-methylbutanoate (10) To a solution of ester 9 (1.32 g, 7.58 mmol) in MeOH (2 mL) was added a solution ofK2CO3 (2.90 g, 21.0 mmol) in H2O/MeOH (20 mL, 7:5) dropwise at 0 C. After 2 h, thereaction mixture was diluted with H2O and extracted with CH2Cl2 (x 5). The combinedorganic layers was dried over MgSO4. Concentrated in vacuo afforded 10 as colorlessoil (970 mg, 5.57 mmol, 73%). [α]D = +1.2 (c 2.12, MeOH), (lit a, [α]D = +1.6 (c 0.01,MeOH)); [α]D = +7.5 (c 1.13, CHCl3), (R)-isomer : (lit b, [α]D = -4.4 (c 0.31, CHCl3)); 1H NMR (300 MHz, CDCl3) δ 3.91 (1H, dd, J = 5.9, 3.3 Hz), 2.75 (1H, d, J = 5.9 Hz),2.10-1.95 (1H, m), 1.50 (9H, s), 1.02 (3H, d, J = 6.9 Hz), 0.86 (3H, d, J = 6.9 Hz);LR-ESI-MS m/z 175 [M+H]+.
With lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 3h;
With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 3h;
With potassium carbonate In methanol; water at 20℃; for 12h;
With ethylenediamine In cyclohexane at 90℃; for 18h; Inert atmosphere;

  • 10
  • [ 17407-55-5 ]
  • [ 3519-30-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 84 percent / 18 h / 20 °C 2: toluene / 3 h / 95 °C 3: LiOH / H2O; methanol; tetrahydrofuran / 3 h / 20 °C
Multi-step reaction with 3 steps 1: 18 h / 20 °C 2: toluene / 3 h / 95 °C 3: aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C
Multi-step reaction with 3 steps 1: 4 h / 60 °C 2: DMAP; DCC / CH2Cl2 / 12 h / 20 °C 3: K2CO3 / methanol; H2O / 12 h / 20 °C
  • 11
  • [ 18667-97-5 ]
  • [ 3519-30-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 3 h / 95 °C 2: LiOH / H2O; methanol; tetrahydrofuran / 3 h / 20 °C
Multi-step reaction with 2 steps 1: toluene / 3 h / 95 °C 2: aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C
Multi-step reaction with 2 steps 1: DMAP; DCC / CH2Cl2 / 12 h / 20 °C 2: K2CO3 / methanol; H2O / 12 h / 20 °C
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C 2: potassium carbonate; water / methanol / 2 h / 0 °C

  • 12
  • [ 3519-30-0 ]
  • [ 125760-11-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature
Multi-step reaction with 7 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature
Multi-step reaction with 7 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature
Multi-step reaction with 7 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature

  • 13
  • [ 3519-30-0 ]
  • [ 13498-70-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature
Multi-step reaction with 2 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2, citric acid / Pd / methanol
  • 14
  • [ 3519-30-0 ]
  • [ 105087-53-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C
Multi-step reaction with 4 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C
  • 15
  • [ 3519-30-0 ]
  • [ 174757-68-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr
Multi-step reaction with 4 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr
  • 16
  • [ 3519-30-0 ]
  • [ 174743-63-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 86 percent / dimethylaminopyridine, DCC / CH2Cl2 / 84 h / 0 °C 4: 99 percent / H2, AcOH / 10percent Pd/C / ethyl acetate / 9 h / Ambient temperature
  • 17
  • [ 3519-30-0 ]
  • [ 174757-67-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature
Multi-step reaction with 3 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature
  • 18
  • [ 3519-30-0 ]
  • [ 174743-71-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 76 percent / dimethylaminopyridine, DCC / CH2Cl2 / 17 h / 0 °C 4: 93 percent / H2, AcOH / 10percent Pd/C / ethyl acetate / 13 h / 0 °C
  • 19
  • [ 3519-30-0 ]
  • benzyloxycarbonyl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleric acid pentafluorophenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 62 percent / DCC, dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 62 percent / DCC, dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
  • 20
  • [ 3519-30-0 ]
  • cyclo-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleryl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature 8: 5 percent / H2, dimethylaminopyridine / 5percent Pd/C / dioxane; ethanol / 90 °C
Multi-step reaction with 8 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature 8: 5 percent / H2, dimethylaminopyridine / 5percent Pd/C / dioxane; ethanol / 90 °C
Multi-step reaction with 8 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature 8: 5 percent / H2, dimethylaminopyridine / 5percent Pd/C / dioxane; ethanol / 90 °C
Multi-step reaction with 8 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / DCC, dimethylaminopyridine / CH2Cl2 / 15 h / Ambient temperature 8: 5 percent / H2, dimethylaminopyridine / 5percent Pd/C / dioxane; ethanol / 90 °C

  • 21
  • [ 3519-30-0 ]
  • benzyloxycarbonyl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature
Multi-step reaction with 6 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature
Multi-step reaction with 6 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature
Multi-step reaction with 6 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature 6: 87 percent / TFA / CH2Cl2 / 3 h / Ambient temperature

  • 22
  • [ 3519-30-0 ]
  • benzyloxycarbonyl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleryl-L-valyl-L-α-hydroxyisovaleric acid t-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / methanol / 5 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 99 percent / TFA / CH2Cl2 / 8 h / 0 °C 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature
Multi-step reaction with 5 steps 1: 99 percent / DCC, dimethylaminopyridine / CH2Cl2 / 24 h / Ambient temperature 2: 100 percent / TFA / CH2Cl2 / 10 h / Ambient temperature 3: 81 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 12 h / Ambient temperature 4: 98 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr 5: 69 percent / DCC, dimethylaminopyridine, N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature

  • 23
  • [ 3519-30-0 ]
  • [ 174743-65-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 86 percent / dimethylaminopyridine, DCC / CH2Cl2 / 84 h / 0 °C 4: 99 percent / H2, AcOH / 10percent Pd/C / ethyl acetate / 9 h / Ambient temperature 5: 55 percent / dimethylaminopyridine, DCC / CH2Cl2 / 72 h / 0 °C 6: 97 percent / TFA / CH2Cl2 / 7.5 h / Ambient temperature
Multi-step reaction with 6 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 86 percent / dimethylaminopyridine, DCC / CH2Cl2 / 84 h / 0 °C 4: 99 percent / TFA / CH2Cl2 / 6 h / Ambient temperature 5: 55 percent / dimethylaminopyridine, DCC / CH2Cl2 / 72 h / 0 °C 6: 97 percent / TFA / CH2Cl2 / 7.5 h / Ambient temperature
  • 24
  • [ 3519-30-0 ]
  • [ 174743-64-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 86 percent / dimethylaminopyridine, DCC / CH2Cl2 / 84 h / 0 °C 4: 99 percent / H2, AcOH / 10percent Pd/C / ethyl acetate / 9 h / Ambient temperature 5: 55 percent / dimethylaminopyridine, DCC / CH2Cl2 / 72 h / 0 °C
Multi-step reaction with 5 steps 1: 84 percent / dimethylaminopyridine, DCC / CH2Cl2 / 20 h 2: 100 percent / TFA / CH2Cl2 / 5 h / Ambient temperature 3: 86 percent / dimethylaminopyridine, DCC / CH2Cl2 / 84 h / 0 °C 4: 99 percent / TFA / CH2Cl2 / 6 h / Ambient temperature 5: 55 percent / dimethylaminopyridine, DCC / CH2Cl2 / 72 h / 0 °C
  • 25
  • [ 3519-30-0 ]
  • [ 1803-69-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd / methanol; acetic acid
Multi-step reaction with 2 steps 1: PhSO2Cl / pyridine 2: H2 / Pd-C
  • 26
  • [ 3519-30-0 ]
  • [ 18671-21-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid
Multi-step reaction with 2 steps 1: PhSO2Cl, Py 2: H2 / PdCl2-C
  • 27
  • [ 3519-30-0 ]
  • [ 3092-13-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd
Multi-step reaction with 2 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2, AcOH / PdO / methanol
  • 28
  • [ 3519-30-0 ]
  • L-Valyl-N-methyl-L-leucyl-L-α-hydroxy-isovaleriansaeure-tert-butylester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd 3: (i) PCl5, (ii) /BRN= 2418531/, Et3N 4: H2 / Pd
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2, AcOH / PdO / methanol 3: (i) PCl5, Et2O, (ii) /BRN= 2418531/, Et3N 4: H2, HCl / PdO / methanol
  • 29
  • [ 3519-30-0 ]
  • D-Valyl-D-leucyl-L-α-hydroxy-isovaleryl-L-valyl-N-methyl-L-leucyl-L-α-hydroxy-isovaleriansaeure [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd 3: (i) Et3N, ClCO2Et, (ii) /BRN= 6132110/ 4: CF3CO2H 5: (i) PCl5, (ii) /BRN= 6133284/, Et3N 6: HBr / acetic acid
Multi-step reaction with 6 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / PdO / methanol 3: (i) ClCO2Et, Et3N, THF, (ii) /BRN= 6132110/ 4: HCl / diethyl ether 5: (i) PCl5, Et2O, (ii) /BRN= 6133284/, Et3N, THF 6: HBr / acetic acid / Ambient temperature
  • 30
  • [ 3519-30-0 ]
  • [ 3092-14-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd 3: (i) Et3N, ClCO2Et, (ii) /BRN= 6132110/
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / PdO / methanol 3: (i) ClCO2Et, Et3N, THF, (ii) /BRN= 6132110/
  • 31
  • [ 3519-30-0 ]
  • [ 3092-15-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd 3: (i) PCl5, (ii) /BRN= 2418531/, Et3N
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2, AcOH / PdO / methanol 3: (i) PCl5, Et2O, (ii) /BRN= 2418531/, Et3N
  • 32
  • [ 3519-30-0 ]
  • Z-L-Ala-L-HyIv-D-Val-D-HyIv-L-Ala-L-HyIv-D-Val-D-HyIv [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417866/, Et3N, benzene 4: H2 / Pd / methanol 5: (i) SOCl2, (ii) /BRN= 2633973/, Et3N, benzene 6: CF3CO2H
Multi-step reaction with 6 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417866/, Et3N, benzene 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2633973/, Et3N, benzene 6: CF3CO2H
  • 33
  • [ 3519-30-0 ]
  • Z-D-Ala-L-HyIv-L-Val-D-HyIv-D-Ala-L-HyIv-L-Val-D-HyIv [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417867/, Et3N, benzene 4: H2 / Pd / methanol 5: (i) SOCl2, (ii) /BRN= 2633974/, Et3N, benzene 6: CF3CO2H
Multi-step reaction with 6 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417867/, Et3N, benzene 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2633974/, Et3N, benzene 6: CF3CO2H
  • 34
  • [ 3519-30-0 ]
  • Z-L-Ala-L-HyIv-D-Val-D-HyIv-L-Ala-L-HyIv-D-Val-D-HyIv-OtBu [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417866/, Et3N, benzene 4: H2 / Pd / methanol 5: (i) SOCl2, (ii) /BRN= 2633973/, Et3N, benzene
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417866/, Et3N, benzene 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2633973/, Et3N, benzene
  • 35
  • [ 3519-30-0 ]
  • Z-D-Ala-L-HyIv-L-Val-D-HyIv-D-Ala-L-HyIv-L-Val-D-HyIv-OtBu [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417867/, Et3N, benzene 4: H2 / Pd / methanol 5: (i) SOCl2, (ii) /BRN= 2633974/, Et3N, benzene
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: TsOH / benzene 3: (i) SOCl2, (ii) /BRN= 2417867/, Et3N, benzene 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2633974/, Et3N, benzene
  • 36
  • [ 3519-30-0 ]
  • NZ-D-Val(Me)-HyiV-D-Val(Me)-HyiV-D-Val(Me)-HyiV-OtBu-d3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) carbonyldiimidazole, CH2Cl2, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 6700597/, Et3N, Et2O
Multi-step reaction with 5 steps 1: (i) carbonyldiimidazole, CH2Cl2, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 6700597/, Et3N, Et2O 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 6700597/, Et3N, Et2O
  • 37
  • [ 3519-30-0 ]
  • NZ-Val(Me)-HyiV-Val(Me)-HyiV [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H
  • 38
  • [ 3519-30-0 ]
  • NZ-D-Val(Me)-HyiV-Val(Me)-HyiV [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H
  • 39
  • [ 3519-30-0 ]
  • NZ-Val(Me)-HyiV-Val(Me)-HyiV-OtBu [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF
  • 40
  • [ 3519-30-0 ]
  • NZ-D-Val(Me)-HyiV-Val(Me)-HyiV-OtBu [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF
  • 41
  • [ 3519-30-0 ]
  • NZ-Val(Me)-D-HyiV-Val(Me)-HyiV-Val(Me)-HyiV-OtBu [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2418093/, Et3N, Et2O
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 2418093/, Et3N, Et2O
  • 42
  • [ 3519-30-0 ]
  • NZ-D-Val(Me)-HyiV-D-Val(Me)-HyiV-Val(Me)-HyiV-OtBu [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 2418093/, Et3N, Et2O
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2809877/, Et3N, THF 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2418093/, Et3N, Et2O
  • 43
  • [ 3519-30-0 ]
  • NZ-Val(Me)-HyiV-Val(Me)-HyiV-D-Val(Me)-HyiV-OtBu [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2809877/, Et3N, Et2O
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) PCl5, Et2O, (ii) /BRN= 2418093/, Et3N, THF 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 2809877/, Et3N, Et2O
  • 44
  • [ 3519-30-0 ]
  • [ 3092-12-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) Py, PhSO2Cl, (ii) /BRN= 4658890/ 2: H2 / Pd
Multi-step reaction with 2 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / PdO / methanol
  • 45
  • [ 3519-30-0 ]
  • NZ-D-Ile(Me)-HyiV-D-Ile(Me)-HyiV-D-Ile(Me)-HyiV-OtBu [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 6699841/, Et3N, Et2O 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 6699841/, Et3N, Et2O
Multi-step reaction with 3 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / Pd-C / methanol; acetic acid 3: (i) SOCl2, (ii) /BRN= 6699841/, Et3N, Et2O
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: CF3CO2H 3: (i) SOCl2, (ii) /BRN= 6699841/, Et3N, Et2O 4: CF3CO2H 5: (i) SOCl2, (ii) /BRN= 6699841/, Et3N, Et2O
  • 46
  • [ 3519-30-0 ]
  • [ 3275-32-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / PdO / methanol 3: (i) ClCO2Et, Et3N, THF, (ii) /BRN= 6132110/ 4: HCl / diethyl ether 5: (i) PCl5, Et2O, (ii) /BRN= 6133284/, Et3N, THF
  • 47
  • [ 3519-30-0 ]
  • [ 3092-24-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) PhSO2Cl, Py, (ii) /BRN= 4658890/ 2: H2 / PdO / methanol 3: (i) ClCO2Et, Et3N, THF, (ii) /BRN= 6132110/ 4: HCl / diethyl ether
  • 48
  • [ 3519-30-0 ]
  • [ 503-38-8 ]
  • (S)-2-(chlorocarbamoyloxy)-3-methylbutyric acid, tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In tetrahydrofuran; diethyl ether 1.A (S)-2-(chlorocarbamoyloxy)-3-methylbutyric acid, tert-butyl ester Method A (S)-2-(chlorocarbamoyloxy)-3-methylbutyric acid, tert-butyl ester To a solution of diphosgene (4.55 g) in THF (34 ml) at 0° C. was added a solution of (S)-2-hydroxy-3-methylbutyric acid tert-butyl ester (for preparation method see Tetrahedron. Lett., (1993), 7409) (4.0 g) and pyridine (1.82 g)in THF (34 ml) dropwise over 25 minutes. The resulting mixture was allowed to warm to room temperature over 4 hours. The mixture was then filtered through celite and the filtrate concentrated under reduced pressure. The residue was re-dissolved in diethyl ether (200 ml) and again filtered through celite. The filtrate was concentrated under reduced pressure to give the sub-title compound as a pale yellow oil (5.27 g): 1H NMR (400 MHz, CDCl3) δ 0.98-1.10 (6H, m), 1.55 (9H, s), 2.30 (1H, m), 4.83 (1H, m).
  • 49
  • [ 358-23-6 ]
  • [ 3519-30-0 ]
  • [ 1059044-37-9 ]
YieldReaction ConditionsOperation in experiment
89% With 2,6-dimethylpyridine In dichloromethane at 0℃; for 0.833333h; Inert atmosphere; optical yield given as %ee;
  • 52
  • [ 94820-26-5 ]
  • [ 3519-30-0 ]
  • (S)-1-(tert-butoxy)-3-methyl-1-oxobutan-2-yl N-((benzyloxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threoninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; (S)-1-(tert-Butoxy)-3-methyl-1-oxobutan-2-yl N-((benzyloxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threoninate (12) To a mixture of alcohol 10 (799 mg, 4.59 mmol), 11 (2.02 g, 5.51 mmol) and DMAP(167 mg, 1.38 mmol) in CH2Cl2 (18 mL) was added a solution of DCC (1.25 g, 6.06mmol) in CH2Cl2 (18 mL) dropwise at 0 C. The reaction mixture was stirred overnightat rt. The reaction mixture was diluted with n-hexane. The resulting mixture was filteredthrough a pad of Celite and concentrated in vacuo. The crude residue was purified byflash column chromatography (7% EtOAc in n-hexane) to give compound 12 ascolorless oil (2.24 g, 4.28 mmol, 93%). [α]D = -23.4 (c 1.1, CHCl3); 1H NMR (300 MHz,CDCl3) δ 7.45-7.30 (5H, m), 5.45 (1H, d, J = 9.6 Hz), 5.14 (2H, s), 4.82 (1H, d, J =4.2Hz), 4.50 (1H, qd, J = 6.2, 2.0 Hz), 4.31 (1H, dd, J = 9.6, 2.0 Hz), 2.25-2.12 (1H, m),1.46 (9H, s), 1.25 (3H, d, J = 6.2 Hz), 0.98 (3H, d, J = 7.0 Hz), 0.96 (3H, d, J = 7.0 Hz),0.83 (9H, s), 0.06 (3H, s), 0.03 (3H, s); 13C NMR (75 MHz, CDCl3) δ 170.53, 167.85,156.49, 136.24, 128.45, 128.13, 128.09, 81.85, 77.24, 68.40, 66.96, 59.70, 30.33, 27.92,25.65, 21.24, 18.60, 17.78, 17.04, -4.55, -5.24; HR-ESI-MS calcd. for C27H46NO7Si524.3038: found 524.3038 [M+H]+.
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