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Chemical Structure| 20312-37-2 Chemical Structure| 20312-37-2
Chemical Structure| 20312-37-2

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(R)-Leucic acid is a metabolite of branched-chain amino acids that shows properties in promoting muscle growth and reducing muscle breakdown.

Synonyms: D-α-Hydroxyisocaproic acid

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Product Details of (R)-Leucic acid

CAS No. :20312-37-2
Formula : C6H12O3
M.W : 132.16
SMILES Code : CC(C)C[C@@H](O)C(O)=O
Synonyms :
D-α-Hydroxyisocaproic acid
MDL No. :MFCD00211263
InChI Key :LVRFTAZAXQPQHI-RXMQYKEDSA-N
Pubchem ID :439960

Safety of (R)-Leucic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of (R)-Leucic acid

* 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 [ 20312-37-2 ]

[ 20312-37-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1342309-23-2 ]
  • [ 17407-56-6 ]
  • [ 17407-55-5 ]
  • [ 312-84-5 ]
  • [ 56-45-1 ]
  • [ 20312-37-2 ]
  • [ 13748-90-8 ]
  • [ 3060-46-6 ]
  • [ 63-91-2 ]
  • [ 31321-74-1 ]
  • [ 673-06-3 ]
  • 2
  • [ 1342309-24-3 ]
  • [ 17407-56-6 ]
  • [ 17407-55-5 ]
  • [ 312-84-5 ]
  • [ 56-45-1 ]
  • [ 20312-37-2 ]
  • [ 13748-90-8 ]
  • [ 3060-46-6 ]
  • [ 63-91-2 ]
  • [ 31321-74-1 ]
  • [ 673-06-3 ]
  • 3
  • [ 20312-37-2 ]
  • [ 41036-32-2 ]
  • C16H23NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 20℃; To a soln of D-Alanine benzyl ester p-toluene sulfonate (58.50 g, 167 mmol) in acetonitrile anhyd (100 mL) was dropwised DIPEA (44.97 g, 348 mmol) in acetonitrile anhyd (50 mL) at 0 C. The mixture was added D-O-leucine (20.00 g, 151 mmol) in acetonitrile anhyd (50 mL), EDCI hydrochloride (34.81 g, 182 mmol) and HOBt (20.45 g, 151 mmol) and stirred at r.t. over night. The reaction mixture was then evaporated concentrated under reduced pressure. The residue was washed sequentially 10% citric acid (3 × 300 mL), sat. NaHCO3 soln (3 × 300 mL) and brine (3 × 300 mL). The organic layer was dried over Na2SO4, filtered and concentrated under redued pressure. The crude residue was purified by silica gel chromatography (hexane-EtOAc, 9:1) and recrystallized from EtOAc-hexane as a white solid; yield: 43.58 g (98%); mp 60.5-61.7 C, [a]D25 +47.29 (c 1.00, CHCl3). IR (KBr film):3385, 3323, 2956, 2870, 1743, 1643, 1529, 1464, 1398, 1294, 1163, 1083, 742, 697. 1H NMR (CDCl3, 400 MHz): delta = 0.94 (d, J=2.4 Hz, 3H), 0.96 (d, J=2.4 Hz, 3H), 1.43 (d, J=7.2 Hz, 3H), 1.43-1.66 (m, 2H), 1.84-1.86 (m, 1H), 2.82 (s, 1H), 4.14-4.17 (m, 1H), 4.63-4.66 (m, 1H), 5.14 (dd, J=12.4, 5.2 Hz, 2H), 6.99 (d, J=11.5 Hz, 1H), 7.33-7.39 (m, 5H). ESI-MS: m/z [M+H]+ calcd for C16H24NO4: 294.1705; found: 294.1737.
 

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