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Chemical Structure| 248921-66-6

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Product Details of Boc-D-Ser(tBu)-OH

CAS No. :248921-66-6
Formula : C12H23NO5
M.W : 261.31
SMILES Code : O=C(O)[C@H](NC(OC(C)(C)C)=O)COC(C)(C)C
MDL No. :MFCD09751020
InChI Key :BPYLRGKEIUPMRJ-MRVPVSSYSA-N
Pubchem ID :6992546

Safety of Boc-D-Ser(tBu)-OH

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

Application In Synthesis of Boc-D-Ser(tBu)-OH

* 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 [ 248921-66-6 ]

[ 248921-66-6 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 248921-66-6 ]
  • [ 56602-33-6 ]
  • [ 86499-35-6 ]
  • [ 77-92-9 ]
  • [ 145486-02-8 ]
YieldReaction ConditionsOperation in experiment
480 mg (100%) With triethylamine; In dichloromethane; ethyl acetate; Step A: 2(R)-t-Butoxycarbonylamino-3-(t-butoxy)-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]propanamide To a solution of 200 mg (1.13 mmol) of 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Example 1, Step B) in 8 mL of dry methylene chloride was added 0.206 mL (1.48 mmol) of triethylamine, 553 mg (1.25 mmol) of <strong>[248921-66-6]BOC-D-serine t-butyl ether</strong> followed by 602 mg (1.36 mmol) of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate. The reaction mixture was stirred at room temperature for 2 hours then diluted with 100 mL of ethyl acetate, washed with 25 mL of 5% aqueous citric acid, 25 mL of saturated sodium bicarbonate and 25 mL of brine. The organic layer was dried over magnesium sulfate, filtered and the solvents removed under vacuum. The residue was purified by flash chromatography on silica gel, eluding with ethyl acetate/hexane (55:45) to afford 480 mg (100%) of the product as a white foam. 1 H NMR (200 MHz,CDCl3): 1.20 (s,9H), 1.47 (s,9H), 1.92 (m,1H), 2.55-3.02 (m,3H), 3.38 (t,8 Hz,1H), 3.78 (m,1H), 4.15 (m,1H), 4.52 (m,1H), 5.45 (s,1H), 7.00 (m,1H), 7.10-7.35 (m,3H), 7.68 (d,4 Hz,1H), 8.05 (s,1H). FAB-MS: calculated for C22 H33 N3 O5 419; found 420 (M+H,20%), 426 (M+Li,40%).
  • 2
  • [ 110-91-8 ]
  • [ 248921-66-6 ]
  • [ 935878-01-6 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 0 - 20℃; STEP A: (l-fe/t-Butoxymethyl-2-morpholin-4-yl-2-oxo-ethyl)-(J?)-carbamic acid fert-butyl ester To an ice cooled solution of morpholine (0.6 mL, 6.9 mmol) , <strong>[248921-66-6]Boc-D-Ser(tBu)-OH</strong> (3 g, 6.8 mmol) and HOBT (1.2 g, 9 mmol) in CH2Cl2 (50 mL), TEA (1.9 mL) was added followed by addition of 1,3-dimethylamino propyl-3-ethylcarbodiimide (EDC, 1.7 g, 8.6 mmol). The reaction mixture was allowed to warm to room temperature and was then stirred overnight. EtOAc (200 mL) was added to the reaction mixture. This resulting solution was washed with dilute HCl solution, NaHCO3 (aq.) solution, and NaCl (aq.) solution. The organic <n="109"/>layer was dried over MgSO4, filtered, and evaporated to yield (l-tert-butoxymethyl-2- morpholin-4-yl-2-oxo-ethyl)-(/?J-carbamic acid tert-butyl ester as a crude oil. MH+ 331.2
  • 3
  • [ 248921-66-6 ]
  • [ 1137085-16-5 ]
  • C32H46N6O12 [ No CAS ]
  • 4
  • [ 248921-66-6 ]
  • [ 74-88-4 ]
  • [ 1126450-26-7 ]
  • 5
  • [ 24424-99-5 ]
  • [ 18783-53-4 ]
  • [ 248921-66-6 ]
  • 7
  • [ 248921-66-6 ]
  • [ 1212336-73-6 ]
  • 8
  • Fmoc-gly-wang resin [ No CAS ]
  • [ 248921-66-6 ]
  • [ 21394-04-7 ]
  • [ 1429504-34-6 ]
  • [ 1429504-44-8 ]
  • [ 71989-14-5 ]
  • [ 35661-38-2 ]
  • [ 109425-55-0 ]
  • (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-N-trityl-succinamic acid [ No CAS ]
  • C122H173N17O32 [ No CAS ]
  • 9
  • [ 248921-66-6 ]
  • [ 1367454-32-7 ]
  • [ 1367455-21-7 ]
YieldReaction ConditionsOperation in experiment
79% 2-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-4,5-difluorobenzyl (R)-3-tert-butoxy-2-tert-butoxycarbonylaminopropionate (?A93?) [0808] 954 mg of dicyclohexylcarbodiimide are added to a solution of 2.4 g of <strong>[248921-66-6](R)-3-tert-butoxy-2-tert-butoxycarbonylaminopropionic acid</strong> in 50 ml of dichloromethane, and the mixture is stirred at 25 C. for 1 h. The precipitate is filtered off, and the filtrate is added to a solution of 1 g of [2-amino-6-(4,5-difluoro-2-hydroxymethylphenyl)quinazolin-4-yl]-(1,3-dihydroisoindol-2-yl)methanone and 14 mg of 4-(dimethylamino)pyridine (DMAP) in 50 ml of tetrahydrofuran. The mixture is stirred at 25 C. for 48 h, undissolved material is filtered off, and the filtrate is evaporated to dryness. The residue is purified by normal-phase chromatography. [0809] Yield: 1.2 g (79%) of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-4,5-difluorobenzyl (R)-3-tert-butoxy-2-tert-butoxycarbonylaminopropionate; LC-MS retention time: 2.79 min.
 

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