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Chemical Structure| 167216-22-0 Chemical Structure| 167216-22-0

Structure of 167216-22-0

Chemical Structure| 167216-22-0

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Product Details of [ 167216-22-0 ]

CAS No. :167216-22-0
Formula : C10H21NO3
M.W : 203.28
SMILES Code : O=C(OC(C)(C)C)NC(C)(C)CCO
MDL No. :MFCD19982636
InChI Key :QHSUFODBDZQCHO-UHFFFAOYSA-N
Pubchem ID :15473340

Safety of [ 167216-22-0 ]

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

Application In Synthesis of [ 167216-22-0 ]

* 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 [ 167216-22-0 ]

[ 167216-22-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 167216-22-0 ]
  • [ 181646-38-8 ]
YieldReaction ConditionsOperation in experiment
56% With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; at 25℃; for 1h; <strong>[167216-22-0](3-Hydroxy-1,1-dimethyl-propyl)-carbamic acid tert-butyl ester</strong> (9.8 g, 0.048 mol) was dissolved in DMSO (160 mL). The solution was treated with Et3N (20.2 mL, 0.145 mol) followed by a solution of pyridine sufurtrioxide complex (23.2 g, 0.145 mol) in DMSO (160 mL). Upon complete addition, the solution was stirred for 1 h at 25 C. The mixture was diluted with brine and extracted with Et2O (3 x 125 mL). The organic phase was washed with 10% citric acid (aq), saturated NaHCO3 and brine. The organic phase was dried (MgSO4) and concentrated to the desired material as a yellow oil (8. 3 g, 56%): 1H NMR (DMSO-d6) δ 9.67 (t, 1H, J = 3 Hz), 2.66 (s, 2H), 1.37 (s, 9H), 1.28 (s, 6H).
With pyridine; triethylamine; In dimethyl sulfoxide; Step 5: (1,1-Dimethyl-3-oxo-propyl)-carbamic acid tert-butyl ester. <strong>[167216-22-0](3-Hydroxy-1,1-dimethyl-propyl)-carbamic acid tert-butyl ester</strong>(9.8 g, 0.048 mol)was dissolved in DMSO(160 mL). The solution was treated with Et3N(20.2 mL, 0.145 mol) followed by a solution of pyridine sufurtrioxide complex(23.15 g, 0.145 mol) in DMSO(160 mL). Upon complete addition, the solution was stirred for 1 h at 25 C. The mixture was diluted with brine and extracted with Et2O(3*125 mL). The organic phase was washed with 10% citric acid(aq), saturated NaHCO3 and brine. The organic was dried(MgSO4) and concentrated to the desired material as a yellow oil(8.3 g, 56%); 1H NMR (DMSO-d6) δ 9.67 (t, J=3 Hz, 1H), δ 2.66 (s, 2H), δ 1.37 (s, 9H), δ 1.28 (s, 6H).
With hydrogenchloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In n-heptane; dichloromethane; ethyl acetate; at -78℃; for 0.583333h; 3-(tert-Butoxycarbonylamino)-3-methylbutanal At -78 C. DMSO (1.22 ml, 17.2 mmol) was added to a solution of oxalyl chloride (1.1 ml, 12.9 mmol) in dichloromethane (15 ml).. The mixture was stirred for 15 min at -78 C. A solution of 3-hydroxy-1,1-dimethylpropylcarbamic acid tert-butyl ester (1.75 g, 8.6 mmol) in dichloromethane (10 ml) was added dropwise over a period of 15 min.. The solution was stirred at -78 C. for another 15 min.. triethylamine (6.0 ml, 43 mmol) was added.. The solution was stirred at -78 C. for 5 min and then warmed to room temp.. The solution was diluted with dichloromethane (100 ml) and extracted with 1N hydrochloric acid (100 ml).. The aqueous phase was extracted with dichloromethane (50 ml).. The combined organic layers were washed with a saturated solution of sodium hydrogencarbonate (100 ml) and dried over magnesium sulfate.. The solvent was removed in vacuo.. The crude product was purified by column chromatography on silica (140 g) with ethyl acetate/heptane (1:3) to give 1.10 g of 3-(tert-butoxycarbonylamino)-3-methylbutanal. 400 MHz-1H-NMR (CDCl3): d=1.39 (s, 6 H); 1.45 (s, 9 H); 2.85 (d, 2 H); 4.73 (br. 1 H); 9.80 (t, 1 H).
With pyridine-SO3 complex; triethylamine; In dimethyl sulfoxide; at 20℃; for 72h; Step 2: tert-butyl (3-amino-1,1-dimethyl-propyl)-carbamate; 38.6 g (242.7 mmol) sulphur trioxide-pyridine complex are added at ambient temperature to 31.9 g (157 mmol) tert-butyl (3-amino-1,1-dimethyl-propyl)-carbamate and 63.3 mL (455 mmol) triethylamine in 400 mL dimethylsulphoxide. The reaction mixture is stirred for 72 hours at ambient temperature and then combined with 200 mL toluene and 300 mL water. The phases are separated and the aqueous phase is extracted with toluene. The combined organic phases are washed successively with aqueous potassium hydrogen sulphate solution (0.5 M), aqueous sodium hydrogen carbonate solution (10% ish) and water, dried on sodium sulphate and concentrated by evaporation in the rotary evaporator.
1.8 g With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 3h; To a solution of the <strong>[167216-22-0]tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate</strong> (2 g, 9.8 mmol) in DCM (18 mL) at 0C was added Dess-Martin periodinane (7.2 g, 17.14 mmol). The reactionmixture was stirred at RT for 3 h. Progress of reaction was monitored TLC. After completion, reaction mixture was quenched with aq. NaHCO3, and extracted with EtOAc (2 x 50 mL). Combined organic layer was washed with brine (2 x 20 mL), dried over sodium sulfate. Removal of solvent gave crude which was purified by silica gel column chromatography using ethyl acetate-hexane as eluent to afford tert-butyl (2-methyl-4-oxobutan-2-yl)carbamate as a yellowsolid (1.8 g).
1.8 g With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 3h; To a solution of the <strong>[167216-22-0]tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate</strong> (2 g, 9.8 mmol) in DCM (18 mL) at 0 C. was added Dess-Martin periodinane (7.2 g, 17.14 mmol). The reaction mixture was stirred at RT for 3 h. Progress of reaction was monitored TLC. After completion, reaction mixture was quenched with aq. NaHCO3, and extracted with EtOAc (2*50 mL). Combined organic layer was washed with brine (2*20 mL), dried over sodium sulfate. Removal of solvent gave crude which was purified by silica gel column chromatography using ethyl acetate-hexane as eluent to afford tert-butyl (2-methyl-4-oxobutan-2-yl)carbamate as a yellow solid (1.8 g).

  • 2
  • C15H27NO6 [ No CAS ]
  • [ 167216-22-0 ]
  • 3
  • C13H23NO6 [ No CAS ]
  • [ 167216-22-0 ]
  • 4
  • [ 42514-50-1 ]
  • [ 24424-99-5 ]
  • [ 167216-22-0 ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane; at 25℃; for 18h; 3-Amino-3-methyl-butan-1-ol (5.0 g, 0.04 mol) was dissolved in 150 mL CH2Cl2 and treated with di-tert-butyl dicarbonate (11.12 g, 0.05 mol). The resulting mixture was stirred for 18 h at 25 C. The mixture was concentrated to the desired material as an amber oil (9.8 g, 100%): 1H NMR (DMSO-d6) δ 3.55 (s, 1H), 4.43 (t, 1H, J = 5 Hz), 3.46 (m, 2H), 1.71 (t, 2H, J = 7 Hz), 1.37 (s, 9H), 1.12 (s, 6H).
100% In ethyl acetate; at 20℃; for 18h; Step 1: tert-butyl (3-hydroxy-1,1-dimethyl-propyl)-carbamate 88.2 g (404 mmol) di-tert.-butyldicarbonate are added batchwise at ambient temperature to a solution of 41.3 g (400 mmol) 3-amino-3-methyl-butanol in 250 mL ethyl acetate. The reaction mixture is stirred for 18 hours at RT and then concentrated by evaporation in the rotary evaporator. 81.3 g (400 mmol, quantitative) tert-butyl (3-amino-1,1-dimethyl-propyl)-carbamate are obtained. Rf=0.48 [silica gel, petroleum ether/ethyl acetate (1/1)] MS [ESI (M+H)+]=204
19% With triethylamine; In tetrahydrofuran; at 20℃; for 16h; To a solution of 3-amino-3-methylbutan-1-ol (4.0 g, 38.8 mmol, CAS42514-50-1) and TEA (3.92 g, 38.8 mmol, 5.4 mL) in THF (50 mL) added dropwise (Boc)2O (9.3 Ig, 9.8 mL, 42.6 mmol) at 20 C. and the mixture was stirred at 20 C. for 16 hours. Once completion, the reaction mixture was quenched by water (15 mL), and then extracted with EA (3×30 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, PE/EA=10:1) to give the title compound (1.50 g, 19% yield) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 4.90 (s, 1H), 3.76 (q, 2H), 2.04 (s, 1H), 1.88 (t, J=6.4 Hz, 2H), 1.43 (s, 9H), 1.32 (s, 6H).
In dichloromethane; b 3-(N-BOC-amino)-3-methyl-butan-1-ol A solution of 24.88 g (0.114 mol) of di-tert-butyl dicarbonate in 70 ml of methylene chloride is added dropwise to a solution of 11.2 g (0.1086 mol) of 3-amino-3-methyl-butan-1-ol [Z. Naturforsch., Teil B, 38, 1146 (1983)] in 70 ml of methylene chloride and the mixture is stirred at room temperature for 90 hours. After evaporation of the reaction mixture in vacuo, the oily title compound is obtained as a crude product, Rf value=0.52 (silica gel/methylene chloride:methanol (9:1)).
In dichloromethane; C (3-Hydroxy-1,1-dimethyl-propyl)-carbamic Acid Tert-Butyl Ester 3-Amino-3-methyl-butan-1-ol (5.0 g, 0.04 mol) was dissolved in 150 mL CH2Cl2 and treated with di-tert-butyl dicarbonate (11.12 g, 0.05 mol). The resulting mixture was stirred for 18 h at 25 C. The mixture was concentrated to the desired material as an amber oil (9.8 g, 100%): 1H NMR (DMSO-d6) δ 3.55 (s, 1H), 4.43 (t, 1H, J=5 Hz), 3.46 (m, 2H), 1.71 (t, 2H, J=7 Hz), 1.37 (s, 9H), 1.12 (s, 6H).
In dichloromethane; Step 4: (3-Hydroxy-1,1-dimethyl-propyl)-carbamic acid tert-butyl ester. 3-Amino-3-methyl-butan-1-ol(5.0 g, 0.04 mol) was dissolved in 150 mL CH2Cl2 and treated with di-tert-butyl dicarbonate(11.12 g, 0.05 mol). The resulting mixture was stirred for 18 h at 25 C. The mixture was concentrated to the desired material as an amber oil(9.8 g, 100%); 1H NMR (DMSO-d6) δ 3.55 (s,1H), δ 4.43 (t, J=5 Hz, 1H), δ 3.46 (m, 2H), δ 1.71 (t, J=7 Hz, 2H), δ 1.37(s, 9H), δ 1.12(s, 6H).
In ethyl acetate; for 1.5h; a. Tert-butyl (3-hvdroxy-1 ,1-dimethylpropyl)-carbamidate200 g (1.94 mol) 3-amino-3-methylbutan-1 -ol in 0.75 I ethyl acetate are combined with a solution of 435.0 g (1.99 mol) di-tert-butyl-dicarbonate in 0.75 I ethyl acetate within one hour. The reaction mixture is stirred for 30 min and the solvent is eliminated in vacuo. The residue obtained is used in the next step without further purification. Yield: 412.5 g1H-NMR (DMSO, 400 MHz): 1.19 (s, 9H); 1.36 (s, 6H); 1.68-1.74 (m, 2H); 3.42-3.50 (m, 2H); 4.39 (t, J = 4.8, 1 H); 6.36 (br s, 1 H).Alternatively, tert-butyl (3-hydroxy-1 ,1-dimethylpropyl)-carbamidate may also be prepared by the methods described for example in J. of Labell. Compounds & Radioph. 2001 , 44(4), 265-275 or WO 03/037327, p. 82/83.
In ethyl acetate; for 1.5h; Component XI [preparation of the compound of formula (IIIb)]N-tert-butoxycarbonyl-4,4-dimethyl-[1,2,3]oxathiazinane-2,2-dioxide a. tert-butyl (3-hydroxy-1,1-dimethylpropyl)-carbamidate 3-amino-3-methylbutan-1-ol (200.0 g, 1.94 mol) is dissolved in ethyl acetate (0.75 l) and within one hour combined with a solution of di-tert-butyl-dicarbonate (435.0 g, 1.99 mol) in ethyl acetate (0.75 l). After the addition has ended the reaction mixture is stirred for another 30 min. After elimination of the solvent the title compound is obtained, which is used in the next step without further purification. Yield: 412.5 g 1H-NMR (DMSO, 400 MHz): 1.19 (s, 9H); 1.36 (s, 6H); 1.68-1.74 (m, 2H); 3.42-3.50 (m, 2H); 4.39 (t, J=4.8, 1H); 6.36 (br s, 1H). Alternatively tert-butyl (3-hydroxy-1,1-dimethylpropyl)-carbamidate may also be prepared using the methods described for example in J. of Labell. Compounds & Radioph. 2001, 44(4), 265-275 or der WO 03/037327, p. 82/83.
In ethyl acetate; for 16h; Intermediate X: 3,3-dimethyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2- a]indole-8-carboxylic acid Step 1: Synthesis of tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate To a solution of 3-amino-3-methylbutan-1-ol (1.0 g, 9.7 mmol) in EtOAc (5 mL) is added di-tert-butyl dicarbonate (2.1 g, 9.7 mmol). The mixture is stirred for 16 h and the solvent is evaporated to afford the crude title compound which is used in the next step without purification
In dichloromethane; at 20℃; for 18h; To a solution of 3-amino-3-methyl-butan-1-ol (5.0 g, 48.54 mmol) in CH2C12 (150 mL) was added di-tert-butyl dicarbonate (13.22 g, 60.27 mmol) at RT and resulting mixture was stirred for 18 h. Progress of reaction was monitored by TLC. After completion, reaction mixture was concentrated under vacuum to afford tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate asan amber oil (9.8 g) which was used in the next step without purification.
Synthesis of tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate Into a 200-mL round-bottom flask under a nitrogen atmosphere, was placed a solution of 3-amino-3- methylbutan-1 -ol (2.5 g, 24.2 mmol, 1 equiv) and TEA (4.9 g, 48.5 mmol, 2 equiv) in anhydrous DCM (50 ml_). The mixture was stirred for 10 minutes at 25C. Then (Boc)20 (5.3 g, 24.2 mmol,1 equiv) was added in one portion. The resulting solution was stirred for 6 hours at 25 C. The reaction was then quenched by the addition of water (20 ml_). The resulting solution was extracted with dichloromethane (3x30 ml.) and the organic layers combined was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuum. This resulted in tert- butyl N-(4-hydroxy-2-methylbutan-2-yl)carbamate which was used in the next step directly.
9.8 g In dichloromethane; at 20℃; for 18h; To a solution of 3-amino-3-methyl-butan-1-ol (5.0 g, 48.54 mmol) in CH2Cl2 (150 mL) was added di-tert-butyl dicarbonate (13.22 g, 60.27 mmol) at RT and resulting mixture was stirred for 18 h. Progress of reaction was monitored by TLC. After completion, reaction mixture was concentrated under vacuum to afford tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate as an amber oil (9.8 g) which was used in the next step without purification.
In dichloromethane; at 25℃; for 12h; tert-Butoxycarbonyl tert-butyl carbonate (1.3 g, 5.8 mmol, 1.3 mL, 1.2 eq) and 3-amino-3-methyl-butan-1-ol (0.5 g, 4.8 mmol, 1 eq in DCM (15 mL) was stirred at 25C for 12 hr. The reaction mixture was concentrated under reduce pressure to give tert-butyl (4- hydroxy-2-methylbutan-2-yl)carbamate

  • 9
  • [ 167216-22-0 ]
  • (E)-5-Amino-5-methyl-hex-2-enoic acid {(R)-2-benzyloxy-1-[methyl-((R)-1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-ethyl}-methyl-amide [ No CAS ]
  • 10
  • [ 167216-22-0 ]
  • (2E)-5-Amino-5-methylhex-2-enoic acid N-methyl-N-((1R)-1-(N-methyl-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)-carbamoyl)-2-(1-naphthyl)ethyl)amide [ No CAS ]
  • 11
  • [ 167216-22-0 ]
  • (E)-5-Amino-5-methyl-hex-2-enoic acid methyl-{(R)-1-[methyl-((R)-1-methylcarbamoyl-2-thiophen-2-yl-ethyl)-carbamoyl]-2-naphthalen-2-yl-ethyl}-amide [ No CAS ]
  • 12
  • [ 167216-22-0 ]
  • [ 193079-69-5 ]
  • 13
  • [ 167216-22-0 ]
  • (2E)-5-Amino-5-methylhex-2-enoic acid N-methyl-N-((1R)-1-(N-methyl-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)carbamoyl)-2-(benzo[b]thiophen-3-yl)ethyl)amide [ No CAS ]
  • 14
  • [ 167216-22-0 ]
  • (E)-5-Amino-5-methyl-hex-2-enoic acid {(R)-1-[((R)-1-ethylcarbamoyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-naphthalen-2-yl-ethyl}-methyl-amide [ No CAS ]
  • 15
  • [ 167216-22-0 ]
  • (E)-5-Amino-5-methyl-hex-2-enoic acid {(R)-2-biphenyl-4-yl-1-[methyl-((R)-1-methylcarbamoyl-2-phenyl-ethyl)-carbamoyl]-ethyl}-methyl-amide [ No CAS ]
  • 16
  • [ 167216-22-0 ]
  • (2E)-5-Amino-5-methylhex-2-enoic acid N-((1R)-1-(N-((1R)-2-(4-fluorophenyl)-1-(methylcarbamoyl)ethyl)-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylamide [ No CAS ]
  • 17
  • [ 167216-22-0 ]
  • (E)-5-Amino-5-methyl-hex-2-enoic acid ((R)-1-[(R)-2-(4-iodo-phenyl)-1-methylcarbamoyl-ethyl]-methyl-carbamoyl}-2-naphthalen-2-yl-ethyl)-methyl-amide [ No CAS ]
  • 18
  • [ 167216-22-0 ]
  • (E)-5-Amino-5-methyl-hex-2-enoic acid ((R)-1-[(R)-2-(3,4-difluoro-phenyl)-1-methylcarbamoyl-ethyl]-methyl-carbamoyl}-2-naphthalen-2-yl-ethyl)-methyl-amide [ No CAS ]
  • 19
  • [ 167216-22-0 ]
  • (E)-5-Amino-5-methyl-hex-2-enoic acid ((R)-1-[(R)-1-((S)-2-hydroxy-propylcarbamoyl)-2-thiophen-2-yl-ethyl]-methyl-carbamoyl}-2-naphthalen-2-yl-ethyl)-methyl-amide [ No CAS ]
  • 20
  • [ 167216-22-0 ]
  • (2E)-5-Amino-5-methylhex-2-enoic acid N-((1R)-1-(N-((1R)-1-((cyclopropylmethyl)carbamoyl)-2-phenylethyl)-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylamide [ No CAS ]
  • 21
  • [ 167216-22-0 ]
  • [ 193085-41-5 ]
  • 22
  • [ 167216-22-0 ]
  • (E)-5-Amino-5-methyl-hex-2-enoic acid methyl-[(R)-1-(methyl-{(R)-2-phenyl-1-[(tetrahydro-furan-2-ylmethyl)-carbamoyl]-ethyl}-carbamoyl)-2-naphthalen-1-yl-ethyl]-amide [ No CAS ]
  • 23
  • [ 167216-22-0 ]
  • [ 193085-77-7 ]
  • 24
  • [ 167216-22-0 ]
  • [ 193085-20-0 ]
  • 25
  • [ 167216-22-0 ]
  • (2E)-5-amino-5-methylhex-2-enoic acid N-((1R)-2-(biphenyl-4-yl)-1-{N-[(1R)-1-((2S)-2-hydroxypropylcarbamoyl)-2-(2-thienyl)ethyl]-N-methylcarbamoyl}ethyl)-N-methylamide [ No CAS ]
  • 26
  • [ 167216-22-0 ]
  • [ 193085-82-4 ]
  • 27
  • [ 167216-22-0 ]
  • (E)-5-Amino-5-methyl-hex-2-enoic acid methyl-[(R)-1-(methyl-{(R)-2-phenyl-1-[(tetrahydro-furan-2-ylmethyl)-carbamoyl]-ethyl}-carbamoyl)-2-naphthalen-2-yl-ethyl]-amide [ No CAS ]
  • 28
  • [ 167216-22-0 ]
  • [ 193086-49-6 ]
  • 29
  • [ 167216-22-0 ]
  • [ 193085-64-2 ]
  • 30
  • [ 167216-22-0 ]
  • [ 213335-90-1 ]
  • 31
  • [ 167216-22-0 ]
  • [ 1027943-26-5 ]
  • 32
  • [ 167216-22-0 ]
  • [ 193085-59-5 ]
  • 33
  • [ 167216-22-0 ]
  • (2E)-5-amino-5-methylhex-2-enoic acid N-((1R)-2-(biphenyl-4-yl)-1-{N-[(1R)-2-(4-fluorophenyl)-1-((2R)-2-hydroxypropylcarbamoyl)ethyl]-N-methylcarbamoyl}ethyl)-N-methylamide [ No CAS ]
  • 34
  • [ 167216-22-0 ]
  • [ 1027547-68-7 ]
  • 35
  • [ 167216-22-0 ]
  • [ 213335-88-7 ]
 

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Technical Information

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