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Chemical Structure| 26782-71-8 Chemical Structure| 26782-71-8
Chemical Structure| 26782-71-8

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H-D-Tle-OH is a tert-leucine (tert-Leu)-containing amino acid derivative that enhances the stability of peptide drugs.

Synonyms: D-a-tert-Butyl-Gly-OH

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Product Details of H-D-Tle-OH

CAS No. :26782-71-8
Formula : C6H13NO2
M.W : 131.17
SMILES Code : N[C@H](C(C)(C)C)C(=O)O
Synonyms :
D-a-tert-Butyl-Gly-OH
MDL No. :MFCD00004265
InChI Key :NPDBDJFLKKQMCM-BYPYZUCNSA-N
Pubchem ID :6950340

Safety of H-D-Tle-OH

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

Application In Synthesis of H-D-Tle-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 [ 26782-71-8 ]

[ 26782-71-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 33105-81-6 ]
  • [ 26782-71-8 ]
  • [ 815-17-8 ]
  • 3
  • [ 33105-81-6 ]
  • [ 17026-42-5 ]
  • [ 26782-71-8 ]
  • L-tert-leucine dibenzoyl-d-tartrate salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; at 28℃; for 24h; Example 1(DL)-tert-Leucine (15 g, 0.1145 mol) was dissolved in water (180 mL).To the solution was added dibenzoyl-d-tartaric acid monohydrate (21.5 g, 0.057 mol) and stirred for 24 hours at 28° C. (±3).The reaction mixture was filtered to collect L-<strong>[33105-81-6]tert-leucine</strong> dibenzoyl-d-tartrate salt.The filtrate was reserved for isolating D-<strong>[33105-81-6]tert-leucine</strong> later.
  • 4
  • [ 26782-71-8 ]
  • [ 33105-81-6 ]
YieldReaction ConditionsOperation in experiment
92% With ammonium hydroxide; at 85℃; for 12h;Autoclave; Example 3Ammonium hydroxide (50 mL, 30percent) solution was placed in an autoclave and D-tert-leucine (5 g) was added.Autoclave was closed and the contents were heated to 85° C. under stirring for 12 hours.After cooling the solution was transferred and concentrated under vacuum at 55° C.The solid residue obtained was stirred with acetone (20 mL), filtered and dried to obtain DL-tert-leucine (4.6 g, 92percent yield, L-isomer: 42percent, D-isomer: 58percent)
With ammonium hydroxide; In water; at 85℃; for 12h;Autoclave; Ammonium hydroxide (50 mL, 30percent) solution was placed in an autoclave and D-tert-leucine (5 g) was added. Autoclave was closed and the contents were heated to 85°C under stirring for 12 hours. After cooling the solution was transferred and concentrated under vacuum at 55°C. The solid residue obtained was stirred with acetone (20 mL), filtered and dried to obtain DL-tert-leucine (4.6 g, 92percent yield, L-isomer: 42percent, D-isomer: 58percent).
  • 5
  • [ 33105-81-6 ]
  • [ 17026-42-5 ]
  • [ 26782-71-8 ]
  • L-tert-leucine dibenzoyl-D-tartrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In water; at 28℃; for 24h;Resolution of racemate; (DL)-tert-Leucine (15 g, 0.1145 mol) was dissolved in water (180 mL). To the solution was added dibenzoyl-d-tartaric acid monohydrate (21.5 g, 0.057 mol) and stirred for 24 hours at 28°C (+/-3). The reaction mixture was filtered to collect L-<strong>[33105-81-6]tert-leucine</strong> dibenzoyl-d-tartrate salt. The filtrate was reserved for isolating D-<strong>[33105-81-6]tert-leucine</strong> later. The tartrate salt was added to water (150 mL) followed by concentrated sulphuric acid (3 mL) and stirred for 4 hours. Liberated dibenzoyl-d-tartaric acid was collected and dried (19.8 g, 92percent yield). The filtrate was washed with diisopropyl ether (50 mL) to remove any traces of dibenzoyl-d-tartaric acid, cooled to 5°C and treated with a saturated solution of barium hydroxide till the pH was neutral. It was filtered to remove the precipitated barium sulphate. The filtrate was concentrated under reduced pressure to remove all the solvent. The residue obtained was stirred with acetone (15 mL x 2), filtered and dried to obtain colorless solid L-<strong>[33105-81-6]tert-leucine</strong> (6 g, 80percent yield, 99percent chemical purity, 99.9percent chiral purity). The filtrate obtained after removing L-<strong>[33105-81-6]tert-leucine</strong> dibenzoyl-d-tartrate salt was concentrated under reduced pressure. The residue obtained was stirred with acetone (15 mL x 2), filtered and dried to obtain colorless solid of D-<strong>[33105-81-6]tert-leucine</strong> (6.37 g, 85percent yield, 98.5percent chemical purity, 98percent chiral purity).
 

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