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Chemical Structure| 89500-39-0 Chemical Structure| 89500-39-0

Structure of 89500-39-0

Chemical Structure| 89500-39-0

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Product Details of [ 89500-39-0 ]

CAS No. :89500-39-0
Formula : C9H17NO5
M.W : 219.24
SMILES Code : O=C(O)C(C)(NC(OC(C)(C)C)=O)CO
MDL No. :MFCD24466110

Safety of [ 89500-39-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 89500-39-0 ]

* 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 [ 89500-39-0 ]

[ 89500-39-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 89500-39-0 ]
  • [ 68176-57-8 ]
  • tert-butyl[1-(5-tert-butyl-1H-benzimidazol-2-yl)-2-hydroxy-1-methylethyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In 1,4-dioxane; at 100℃; for 4h; Preparation 26 tert-Butyl Gamma(1 S)-1 -(5-fe/f-butyl-1 H-benzimidazol-2-yl)-2-hvdroxy-1 - methylethyllcarbamate and fe/f-butyl [(1 R)-1 -(5-fe/f-butyl-1 H-benzimidazol-2-yl)-2- hydroxy-1 -methylethyllcarbamate and To a stirred solution of Rac-N-Boc-2-methylserine (Preparation 53, 700 mg, 3.19 mmol) in dioxane (30 ml_) was added 4-ieri-butyl-1 ,2-diaminobenzene (787 mg, 4.79 mmol), T3P (2130 mg, 3.35 mmol) and TEA (0.89 ml_, 6.39 mmol) and the reaction heated to 100°C for 4 hours. The reaction was cooled and partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic layer was collected and concentrated in vacuo. The residue was first purified using silica gel column chromatography eluting with 2/8 to 0/1 hepatane in TBDME followed by chiral separation using a Chiralpak-IC column, 220 nM eluting with heptanes:iPrOH 80:20 to afford two enantiomers: Peak 1 : 1 1 .24 minutes, 89percent ee Peak 2: 16.94 minutes, 99percent ee. Peak 1 was taken through to the next step and assumed (S).
  • 2
  • [ 89500-39-0 ]
  • [ 68176-57-8 ]
  • [ 1449475-31-3 ]
  • tert-butyl (R)-(2-(5-(tert-butyl)-1H-benzo[d]imidazol-2-yl)-1-hydroxypropan-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In 1,4-dioxane; at 100℃; for 4h; To a stirred solution of 2-((tert-butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoic acid (700 mg, 3.19 mmol) in dioxane (30 mL) was added 4-tert-butyl-1, 2-diaminobenzene (787 mg, 4.79 mmol), T3P (2130 mg, 3.35 mmol) and TEA (0.89 mL, 6.39 mmol) and the reaction heated to 100C for 4 hours. The reaction was cooled and partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic layer was collected and concentrated in vacuo. The residue was first purified using silica gel column chromatography eluting with 2/8 to 0/1 heptane in MTBE followed by chiral separation using a Chiralpak-IC column, 220 nM eluting with heptanes:iPrOH 80:20 to afford two enantiomers: Peak 1: 11.24 minutes, 89percent ee tert-butyl (S)-(2-(5-(tert-butyl)-1H-benzo[d]imidazol-2-yl)-1-hydroxypropan-2-yl)carbamate. Peak 2: 16.94 minutes, 99percent ee. tert-butyl (R)-(2-(5-(tert-butyl)-1H-benzo[d]imidazol-2-yl)-1-hydroxypropan-2-yl)carbamate.
 

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