Name: 124883-99-4|6-((tert-Butyldimethylsilyl)oxy)hexan-1-amine|97%
Brand: Ambeed
SKU: A590008
Price: 47.0 USD
Availability: InStock
Rating: 99 (22 reviews)

1
[ 57378-70-8 ]
[ 124883-99-4 ]
[ 124884-00-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In pyridine for 48h;

Reference： [1]Pon, Richard T. [Tetrahedron Letters, 1991, vol. 32, # 14, p. 1715 - 1718]

2
[ 4048-33-3 ]
[ 18162-48-6 ]
[ 124883-99-4 ]

Yield	Reaction Conditions	Operation in experiment
99.3%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 18h;	Step-1: Synthesis of compound 3 To a solution of 6-aminohexanol (1) (1 eq.) in DCM (500 mL) was added DMAP (0.1 eq.) at ambient temperature and reaction mixture was cooled to 0 °C. Triethyl amine (1.5 eq.) and tert-butyldimethylsilyl chloride (1.2 eq) were added sequentially. Reaction mixture was allowed to come to ambient temperature and stirred at same temperature for 18 h. TLC (10 % methanol in DCM, stain visualization-ninhydrin) showed that starting material was consumed. After completion, reaction mixture was concentrated under vacuum and suspension was filtered off. Filterate was concentrated under reduced pressure to afford 6-((tert-butyldimethylsilyl)oxy)hexan-1-amine (3). Yield: 99.3 %; colourless oil which was used as such for further reactions LC-MS (ESI) m/z calculated for C16H30N30SiCl (M + H)+: 231.20. 1HNMR (400 MHz, chloroform-d1): δ 5.80-5.60 (s, b, 2H), 3.60 (s, 2H), 2.83-2.88 (m, 2H), 1.66 (m, 2H), 1.28-1.54 (m, 6H), 0.83 (br, s, 9H), 0.00 (s, 6 H); 13C NMR (101 MHz, DMSO-d6): δ 63.0, 41.5, 32.7, 32.5, 25.9, 25.9, 25.5, 18.2, 18.2, 18.2, 5.4, 5.4; Anal. calcd. (%) for C12H29NOSi: C, 62.27; H, 12.63; N, 6.05; found (%): C, 62.39; H, 12.56; N, 6.07.
95%	With dmap In dichloromethane at 20℃; for 15h;	Et3N (45.0 mL, 323 mmol) and TBSCI (38.8 g, 257 mmol) were added sequentially to a stirred solution of 6-aminohexanol 101 (25.0 g, 213 mmol) and DMAP (3.00 g, 24.6 mmol) in CH2CI2 (375 mL) at rt. The reaction was stirred for 15 h at rt whereupon it was judged complete by TLC (CH2Cl2/MeOH, 9:1 , stained ninhydrin dip). The mixture was concentrated under vacuum, dissolved in Et20 (250 mL) and washed with sat. aq. NaHC03 (3 x 200 mL) and brine (200 mL). The isolated organic layer was dried over Na2S04, filtered and concentrated to a crude yellow oil. Purification of the crude material was achieved by flash chromatography on silica gel (eluting CH2CI2 to CH2Cl2/MeOH, 9: 1 ) to afford the desired silyl ether 102 (47 g, 95%) as a colourless oil; 1H NMR (CDCI3, 400 MHz) δ 3.46 (2H, t, J = 6.5 Hz, CH2-C1 ), 3.24 (2H, bs, NH2), 2.55 (2H, m, CH2-C6), 1 .36 (4H, m, CH2-C5 and CH2-C6), 1 .20 (4H, m, CH2-C4 and CH2-C3), 0.74 (9H, s, CHs-'BuSi), 0.00 (6H, s, CH3-MeSi); 13C NMR (CDCI3, 100 MHz) δ 63.0 (CH2-C1 ), 41 .5 (CH2-C6), 32.7 (CH2-C2), 32.5 (CH2-C5), 25.9 (CH2-C3 and CH2-C4), 25.54 (CHs-'BuSi), 18.25 C-'BuSi), 5.4 (CHs-MeSi).
86%	In pyridine

11.2 g

With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;

Reference： [1]Sharma, Vijay Kumar; Barde, Anup; Rattan, Sunita [Asian Journal of Chemistry, 2020, vol. 32, # 5, p. 1101 - 1108]
[2]Current Patent Assignee: LINK TECHNOLOGIES - WO2015/132577, 2015, A1 Location in patent: Page/Page column 40-41
[3]Pon, Richard T. [Tetrahedron Letters, 1991, vol. 32, # 14, p. 1715 - 1718]
[4]Salunkhe, Manikrao; Wu, Taifeng; Letsinger, Robert L. [Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8768 - 8772]

3
[ 124883-99-4 ]
[ 100-20-9 ]
[ 144002-77-7 ]

Yield	Reaction Conditions	Operation in experiment
0.704 g	With potassium carbonate In diethyl ether; water; benzene

Reference： [1]Salunkhe, Manikrao; Wu, Taifeng; Letsinger, Robert L. [Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8768 - 8772]

4
[ 124883-99-4 ]
[ 174759-66-1 ]
(2S,3S)-3-{(S)-1-[6-(tert-Butyl-dimethyl-silanyloxy)-hexylcarbamoyl]-3-methyl-butylcarbamoyl}-oxirane-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 0 - 23℃;

Reference： [1]Roush, William R.; Hernandez, Alejandro Alvarez; Zepeda, Gerardo [Synthesis, 1999, # SPEC. ISS., p. 1500 - 1504]

5
[ 124883-99-4 ]
[ 245660-14-4 ]
(2S,3S)-3-{(S)-1-[6-(tert-Butyl-dimethyl-silanyloxy)-hexylcarbamoyl]-3-phenyl-propylcarbamoyl}-oxirane-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 0 - 23℃;

Reference： [1]Roush, William R.; Hernandez, Alejandro Alvarez; Zepeda, Gerardo [Synthesis, 1999, # SPEC. ISS., p. 1500 - 1504]

6
[ 124883-99-4 ]
[ 244214-15-1 ]
[ 244214-16-2 ]

Yield	Reaction Conditions	Operation in experiment
61%	With diethylcarbamazine In pyridine

Reference： [1]Zhao, Zhengyun; Ackroyd, John [Nucleosides and Nucleotides, 1999, vol. 18, # 6-7, p. 1231 - 1234]

7
[ 124883-99-4 ]
[ 144002-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 0.704 g / K₂CO₃ / benzene; diethyl ether; H₂O 2: 40 percent / Bu₄NF / tetrahydrofuran / 1 h

Reference： [1]Salunkhe, Manikrao; Wu, Taifeng; Letsinger, Robert L. [Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8768 - 8772]

8
[ 124883-99-4 ]
[ 144002-82-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 0.704 g / K₂CO₃ / benzene; diethyl ether; H₂O 2: 40 percent / Bu₄NF / tetrahydrofuran / 1 h 3: 65 percent / pyridine, 4-(dimethylamino)pyridine 4: 98 percent / Bu₄NF / tetrahydrofuran / 3 h

Reference： [1]Salunkhe, Manikrao; Wu, Taifeng; Letsinger, Robert L. [Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8768 - 8772]

9
[ 124883-99-4 ]
[ 144002-79-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 0.704 g / K₂CO₃ / benzene; diethyl ether; H₂O 2: 40 percent / Bu₄NF / tetrahydrofuran / 1 h 3: 65 percent / pyridine, 4-(dimethylamino)pyridine

Reference： [1]Salunkhe, Manikrao; Wu, Taifeng; Letsinger, Robert L. [Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8768 - 8772]

10
[ 124883-99-4 ]
[ 144002-84-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 0.704 g / K₂CO₃ / benzene; diethyl ether; H₂O 2: 40 percent / Bu₄NF / tetrahydrofuran / 1 h 3: 65 percent / pyridine, 4-(dimethylamino)pyridine 4: 98 percent / Bu₄NF / tetrahydrofuran / 3 h 5: 60 percent / diisopropylamine, 4-(dimethylamino)pyridine / tetrahydrofuran / 4 h

Reference： [1]Salunkhe, Manikrao; Wu, Taifeng; Letsinger, Robert L. [Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8768 - 8772]

11
[ 124883-99-4 ]
[ 144002-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 0.704 g / K₂CO₃ / benzene; diethyl ether; H₂O 2: 40 percent / Bu₄NF / tetrahydrofuran / 1 h 3: 65 percent / pyridine, 4-(dimethylamino)pyridine 4: 98 percent / Bu₄NF / tetrahydrofuran / 3 h 5: 1.) imidazole, PCl₃, Et₃N, 2.) water / 1.) MeCN, 4 h, 2.) MeCN, 30 min

Reference： [1]Salunkhe, Manikrao; Wu, Taifeng; Letsinger, Robert L. [Journal of the American Chemical Society, 1992, vol. 114, # 23, p. 8768 - 8772]

12
[ 124883-99-4 ]
[ 135137-86-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 81 percent / 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / pyridine / 48 h 2: 88 percent / 4-dimethylaminopyridine / pyridine 3: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h

Reference： [1]Pon, Richard T. [Tetrahedron Letters, 1991, vol. 32, # 14, p. 1715 - 1718]

13
[ 124883-99-4 ]
[ 135137-85-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 81 percent / 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / pyridine / 48 h 2: 88 percent / 4-dimethylaminopyridine / pyridine

Reference： [1]Pon, Richard T. [Tetrahedron Letters, 1991, vol. 32, # 14, p. 1715 - 1718]

14
[ 124883-99-4 ]
<1-N-(4,4'-Dimethoxytrityl)-biotinyl-6-aminohexyl>-2-cyanoethyl-N,N-diisopropylaminophosphoramidite [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 81 percent / 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / pyridine / 48 h 2: 88 percent / 4-dimethylaminopyridine / pyridine 3: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h 4: 81 percent / diisopropylethylamine / CHCl₃ / 1 h / Ambient temperature

Reference： [1]Pon, Richard T. [Tetrahedron Letters, 1991, vol. 32, # 14, p. 1715 - 1718]

15
[ 124883-99-4 ]
[ 141-78-6 ]
[ 1584224-42-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With lanthanum(lll) triflate at 20℃; for 24h; Inert atmosphere; chemoselective reaction;

Reference： [1]Morimoto, Hiroyuki; Fujiwara, Risa; Shimizu, Yuhei; Morisaki, Kazuhiro; Ohshima, Takashi [Organic Letters, 2014, vol. 16, # 7, p. 2018 - 2021]

16
[ 63220-36-0 ]
[ 124883-99-4 ]
[ 1581260-78-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	In ethyl acetate for 0.5h; Cooling with ice;

Reference： [1]Maki, Toshikatsu; Tsuritani, Takayuki; Yasukata, Tatsuro [Organic Letters, 2014, vol. 16, # 7, p. 1868 - 1871]

17
[ 124883-99-4 ]
C₁₄H₂₀N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: calcium chloride / tetrahydrofuran; methanol / 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.25 h / 20 °C

Reference： [1]Current Patent Assignee: LINK TECHNOLOGIES - WO2015/132577, 2015, A1

18
[ 881-86-7 ]
[ 124883-99-4 ]
C₂₀H₃₄N₂O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With calcium chloride; In tetrahydrofuran; methanol; at 20℃;	Dimethyl 2,5-pyridine dicarboxylate 103 (5.00 g, 25.6 mmol) was suspended in a mixture of THF (55 mL) and MeOH (105 mL) in a 500 mL RBF. Calcium chloride (1 1 .4 g, 102 mmol) was added in a single portion and the mixture stirred at rt for 5 mins. TBS-aminohexanol 102 (7.10 g, 30.7 mmol) was then added via syringe over 10 mins and the reaction stirred at rt overnight. The solution was concentrated in vacuo to give a yellow gum which was dissolved in EtOAc (150 mL) and washed with deionised water (150 mL). The aqueous phase was back-extracted with EtOAc (100 mL) and combined organic phases dried over Na2SO4. (0319) Filtration and concentration afforded a pale yellow, opaque oil. Purification of the crude product was achieved by flash chromatography on silica gel (eluting hexane/EtOAc, 85:15) to afford a colourless oil. On drying under vacuum overnight the desired amide 104 was isolated as waxy white solid (5.41 g, 53percent); Rf 0.62 (hexane/EtOAc, 4: 1 , KMnO4 stain); 1H NMR (500 MHz, CDCI3) delta 9.10 (1 H, dd, J = 2.1 , 0.9 Hz, CH-C12), 8.41 (1 H, dd, J = 8.2, 2.1 Hz, CH-C10), 8.25 (1 H, dd, J = 8.2, 0.9 Hz, CH-C9), 8.06 (1 H, br s, NH amide) 3.95 (3H, s, CH3-C14), 3.57 (2H, t, J = 6.5 Hz, CH2-C1 ), 3.46 (2H, dt, J = 7.1 , 6.5 Hz, CH-C6), 1 .67-1 .60 (2H, m, CH2-C2), 1 .54-1 .47 (2H, m, CH2-C5), 1 .43-1 .32 (4H, m, CH2-C3 and CH2-C4), 0.86 (9H, s, CHs-'BuSi), 0.01 (6H, s, CH3-MeSi); 13C NMR (125 MHz, CDCI3) delta 165.2 (C-C13), 163.3 (C-C7), 153.1 (C-C8), 149.4 (CH-C12), 138.7 (CH-C10), 128.0 (C-C1 1 ), 121 .9 (CH-C9), 63.2 (CH2-C1 ), 52.7 (CH3-C14), 39.7 (CH2- C6), 32.8 (CH2-C2), 29.7 (CH2-C5), 26.9 (CH2-C3), 26.1 (CHs-'BuSi), 25.7 (CH2-C4), 18.4 (C-'BuSi), -5.18 (CH3-MeSi).

Reference： [1]Patent: WO2015/132577,2015,A1 .Location in patent: Page/Page column 41-42

19
[ 4048-33-3 ]
[ 124883-99-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: toluene / 4.25 h / 100 °C 2: triethylamine / dichloromethane / 4.58 h / 0 °C 3: hydrazine hydrate / ethanol / 16 h / 20 °C

Reference： [1]Current Patent Assignee: EMERGENT BIOSOLUTIONS INC - WO2016/73652, 2016, A1

20
[ 20274-69-5 ]
[ 124883-99-4 ]
C₁₉H₃₄N₂O₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
600 mg	With triethylamine; In 1,4-dioxane; at 80℃; for 16h;	5 (2.0 g, 8.65 mmol), 1,4-dioxane (30 mL), TEA (3.0 eq), 6 (0.8 eq) at RT; resulting reaction mixture was gradually warmed to 80C for 10 mm and stirred for 16 h. One polar product was observed by TLC. The reaction was quenched with water and extracted with EtOAc (2X50 mL). The combined organic layer was washed with water and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by silica gel column chromatography [100-200 mesh, eluting with 50% EtOAc-hexanej to afford 600 mg of 7 as yellow color thick syrup.

Reference： [1]Patent: WO2016/73652,2016,A1 .Location in patent: Page/Page column 93; 94

21
[ 63945-11-9 ]
[ 124883-99-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 4.58 h / 0 °C 2: hydrazine hydrate / ethanol / 16 h / 20 °C

Reference： [1]Current Patent Assignee: EMERGENT BIOSOLUTIONS INC - WO2016/73652, 2016, A1

22
C₂₀H₃₁NO₃Si [ No CAS ]
[ 124883-99-4 ]

Yield	Reaction Conditions	Operation in experiment
2 g	With hydrazine hydrate In ethanol at 20℃; for 16h;	31 Preparation of 5: Preparation of 5:4 (4.0 g, 11.08 mmol), EtOH (80 mL), NH2NH2.H20 (5.0 eq), RT, 16 h. Starting material was completely consumed and a polar product was observed by TLC. The volatiles were concentrated under reduced pressure and obtained residue was diluted with ice-cold water and extracted with EtOAc (2X60 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford 2.0 g of 5 as colorless thick syrup.

Reference： [1]Current Patent Assignee: EMERGENT BIOSOLUTIONS INC - WO2016/73652, 2016, A1 Location in patent: Page/Page column 93; 94

23
[ 124883-99-4 ]
(2R,3R,4R,5S)-1-(6-((4-((dimethylamino)methyl)-2-nitrophenyl)amino)hexyl)-2-(hydroxymethyl)piperidine-3,4,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: triethylamine / 1,4-dioxane / 16 h / 80 °C 2: triethylamine / dichloromethane / 2.33 h / 0 - 20 °C 3: tetrahydrofuran / 2.17 h / 60 °C / Sealed tube 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 5: oxalyl dichloride / tetrahydrofuran; dimethyl sulfoxide / 4 h / -78 - 20 °C 6: sodium cyanoborohydride / acetic acid / 16 h / 20 °C

Reference： [1]Current Patent Assignee: EMERGENT BIOSOLUTIONS INC - WO2016/73652, 2016, A1

24
[ 124883-99-4 ]
C₂₀H₃₆N₂O₆SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / 1,4-dioxane / 16 h / 80 °C 2: triethylamine / dichloromethane / 2.33 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: EMERGENT BIOSOLUTIONS INC - WO2016/73652, 2016, A1

25
[ 124883-99-4 ]
C₂₁H₃₉N₃O₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / 1,4-dioxane / 16 h / 80 °C 2: triethylamine / dichloromethane / 2.33 h / 0 - 20 °C 3: tetrahydrofuran / 2.17 h / 60 °C / Sealed tube

Reference： [1]Current Patent Assignee: EMERGENT BIOSOLUTIONS INC - WO2016/73652, 2016, A1

26
[ 124883-99-4 ]
C₁₅H₂₅N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / 1,4-dioxane / 16 h / 80 °C 2: triethylamine / dichloromethane / 2.33 h / 0 - 20 °C 3: tetrahydrofuran / 2.17 h / 60 °C / Sealed tube 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C

Reference： [1]Current Patent Assignee: EMERGENT BIOSOLUTIONS INC - WO2016/73652, 2016, A1

27
[ 124883-99-4 ]
C₁₅H₂₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: triethylamine / 1,4-dioxane / 16 h / 80 °C 2: triethylamine / dichloromethane / 2.33 h / 0 - 20 °C 3: tetrahydrofuran / 2.17 h / 60 °C / Sealed tube 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 5: oxalyl dichloride / tetrahydrofuran; dimethyl sulfoxide / 4 h / -78 - 20 °C

Reference： [1]Current Patent Assignee: EMERGENT BIOSOLUTIONS INC - WO2016/73652, 2016, A1

28
[ 124883-99-4 ]
tert-butyl 4-(6-((6-((tert-butyldimethylsilyl)oxy)hexyl)amino)pyrimidin-4-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / ethanol / 18 h / 0 - 20 °C 2: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Sealed tube; Inert atmosphere