Name: 929-10-2|6-Methylheptanoic acid|95%
Brand: Ambeed
SKU: A131300
Price: 22.0 USD
Availability: InStock
Rating: 90 (26 reviews)

1
[ 929-10-2 ]
[ 1653-40-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
	With lithium aluminium tetrahydride

Reference： [1]Tate, Daniel J.; Anemian, Remi; Bushby, Richard J.; Nanan, Suwat; Warriner, Stuart L.; Whitaker, Benjamin J. [Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 120 - 128]
[2]Milburn; Truter [Journal of the Chemical Society, 1954, p. 3344,3347]

2
[ 24286-45-1 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In ethanol

Reference： [1]Julia,S. et al. [Bulletin de la Societe Chimique de France, 1962, p. 1952 - 1959]

3
[ 5212-67-9 ]
[ 929-10-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1962,p. 1952 - 1959

4
[ 929-10-2 ]
[ 5680-80-8 ]
[ 157756-17-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With ammonia; dicyclohexyl-carbodiimide In dichloromethane for 10h;

Reference： [1]Schmidt; Schmidt [Synthesis, 1994, # 3, p. 300 - 304]

5
[ 929-10-2 ]
[ 70767-37-2 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With phosgene at 50℃; for 13h;	5 This embodiment also provides a method for synthesizing an acid chloride using the catalyst, which includes the following steps: preparing a semi-finished product, mixing 267 g of isooctanoic acid and 2.0 g of a catalyst, and then heating to 50° C. and introducing 227 g of phosgene to react for 13 hours, cooling to room temperature to obtain an acid chloride mixture Finished product preparation Nitrogen gas is blown into the acid chloride mixture for 4-6 hours to remove unreacted phosgene and acid gas in the acid chloride mixture to obtain a finished product of isooctanoyl chloride.After testing, the yield of the finished isooctanoyl chloride prepared by this method is 92.1%, and the mass fraction of the isooctanoyl chloride in the finished product is 98.1%.
85%	With thionyl chloride; N,N-dimethyl-formamide for 24h; Ambient temperature;
84.32%	With phosgene In toluene Reflux; Green chemistry;	7 Example 7 Isooctanoic acid (100 g, 0.69 mol) was placed in the reactor,Toluene (100 g) was added, heated to reflux,Phosgene (342.95 g, 3.46 mol) was allowed to react,The product content of 95.13% after cooling down to room temperature, through the residual nitrogen and phosgene and hydrogen chloride net, the first vacuum distillation of the solvent, and then vacuum distillation isooctanoyl chloride 95.11g, yield 84.32%, content 96.89% .

81.5%	With phosgene; diethyl-pyridin-4-yl-amine at 40 - 90℃;	4 Example 4 Preparation of isooctanoyl chloride catalyzed by 4 - diethylaminopyridine150 g of isooctanoic acid and 1.5 g of 4-diethylaminopyridine were charged into the reaction bottle and maintained at a temperature of 40 to 90 ° C. The phosgene reaction was conducted to the reaction flask until the molar ratio of isooctanoic acid to phosgene was 1 : 10:00, stop the phosgene, vacuum distillation to be isooctanoyl chloride, the chemical titration analysis of more than 98%, the molar yield of 81.5%.
	With thionyl chloride Yield given;
9.54 g	With thionyl chloride; N,N-dimethyl-formamide at 20℃; for 24h;
	With thionyl chloride; N,N-dimethyl-formamide at 20℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: KAIFENG HUARUI CHEMICAL MAT - CN107413380, 2020, B Location in patent: Paragraph 0038-0042
[2]Crawforth, James M.; Fawcett, John; Rawlings, Bernard J. [Journal of the Chemical Society. Perkin transactions I, 1998, # 10, p. 1721 - 1725]
[3]Current Patent Assignee: TIANJIN JINGYE FINE CHEMICALS - CN105585478, 2016, A Location in patent: Paragraph 0042; 0043
[4]Current Patent Assignee: TIANJIN JINGYE FINE CHEMICALS - CN105601502, 2016, A Location in patent: Paragraph 0049; 0050; 0051
[5]Marczak; Wicha [Tetrahedron Letters, 1993, vol. 34, # 41, p. 6627 - 6630]
[6]Chavan, Subhash P.; Pasupathy; Shivasankar [Synthetic Communications, 2004, vol. 34, # 3, p. 397 - 404]
[7]Morin, Jesse B.; Adams, Katherine L.; Sello, Jason K. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 8, p. 1517 - 1520]

6
[ 929-10-2 ]
[ 1738-72-3 ]
[ 214753-76-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 8h;

Reference： [1]Sin, Ny; Meng, Lihao; Auth, Hak; Crews, Craig M. [Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 8, p. 1209 - 1217]

7
[ 2788-84-3 ]
[ 929-10-2 ]
[ 157756-17-7 ]

Yield	Reaction Conditions	Operation in experiment
1.43 g	With dicyclohexyl-carbodiimide In dichloromethane at -21 - 20℃; for 12h;

Reference： [1]Bennacer, Bibia; Trubuil, Dominique; Rivalle, Christian; Grierson, David S. [European Journal of Organic Chemistry, 2003, # 23, p. 4561 - 4568]

8
[ 62337-58-0 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium hydroxide In ethanol for 2h; Heating;

Reference： [1]Bennacer, Bibia; Trubuil, Dominique; Rivalle, Christian; Grierson, David S. [European Journal of Organic Chemistry, 2003, # 23, p. 4561 - 4568]

9
[ 1653-40-3 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hydroxide In acetonitrile at 70℃;
	With chromium(VI) oxide; sulfuric acid In water; acetone at 0 - 20℃; for 8h;
86 %Chromat.	With water; potassium carbonate at 80℃;

Multi-step reaction with 2 steps 1.1: zinc(II) oxide; sodium hydroxide / 240 °C / 22502.3 Torr / Inert atmosphere; Autoclave; Large scale 1.2: 0.5 h / 150 °C / 760.05 Torr / Large scale 2.1: chloroacetic acid / water / 0.5 h / 40 °C / Large scale

Reference： [1]Hosseinzadeh, Shahram Zare; Babazadeh, Mirzaagha; Shahverdizadeh, Gholam Hossein; Hosseinzadeh-Khanmiri, Rahim [New Journal of Chemistry, 2019, vol. 43, # 24, p. 9491 - 9499]
[2]Chavan, Subhash P.; Pasupathy; Shivasankar [Synthetic Communications, 2004, vol. 34, # 3, p. 397 - 404]
[3]Vessally, Esmail; Ghasemisarabbadeih, Mostafa; Ekhteyari, Zeynab; Hosseinzadeh-Khanmiri, Rahim; Ghorbani-Kalhor, Ebrahim; Ejlali, Ladan [RSC Advances, 2016, vol. 6, # 108, p. 106769 - 106777]
[4]Current Patent Assignee: TAIAN HAVAY CHEMICALS - CN106278875, 2017, A

10
[ 34452-36-3 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 81 percent / H₂ / Raney nickel / methanol / 20 °C / atmospheric pressure 2: chromium trioxide; H₂SO₄ / H₂O; acetone / 8 h / 0 - 20 °C

Reference： [1]Chavan, Subhash P.; Pasupathy; Shivasankar [Synthetic Communications, 2004, vol. 34, # 3, p. 397 - 404]

11
[ 107-82-4 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: LiNH₂; Fe(NO₃)2 / liquid ammonia / 0.17 h / -33 °C 1.2: 61 percent / liquid ammonia / 6 h / -33 °C 2.1: 81 percent / H₂ / Raney nickel / methanol / 20 °C / atmospheric pressure 3.1: chromium trioxide; H₂SO₄ / H₂O; acetone / 8 h / 0 - 20 °C

Reference： [1]Chavan, Subhash P.; Pasupathy; Shivasankar [Synthetic Communications, 2004, vol. 34, # 3, p. 397 - 404]

12
[ 112182-00-0 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / Pd/C / ethyl acetate / 3.5 h / 20 °C / 3040.2 Torr 2: 69 percent / aq. KOH / ethanol / 2 h / Heating

Reference： [1]Bennacer, Bibia; Trubuil, Dominique; Rivalle, Christian; Grierson, David S. [European Journal of Organic Chemistry, 2003, # 23, p. 4561 - 4568]

13
[ 929-10-2 ]
Dihydroeponemycin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 82 percent / HBTU; Et₃N / CH₂Cl₂ / 8 h / 20 °C 2: 92 percent / imidazole / tetrahydrofuran / 24 h / 20 °C 3: 99 percent / H₂ / Pd-C / methanol / 2 h / 20 °C 4: 78 percent / HATU; i-Pr₂NEt / CH₂Cl₂ / 10 h / 20 °C 5: 86 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

Reference： [1]Sin, Ny; Meng, Lihao; Auth, Hak; Crews, Craig M. [Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 8, p. 1209 - 1217]

14
[ 929-10-2 ]
(S)-O-tert-butyldimethylsiloxymethyl-N-(6-methylheptanoyl)serine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 82 percent / HBTU; Et₃N / CH₂Cl₂ / 8 h / 20 °C 2: 92 percent / imidazole / tetrahydrofuran / 24 h / 20 °C 3: 99 percent / H₂ / Pd-C / methanol / 2 h / 20 °C

Reference： [1]Sin, Ny; Meng, Lihao; Auth, Hak; Crews, Craig M. [Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 8, p. 1209 - 1217]

15
[ 929-10-2 ]
(4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tert-butyldiphenylsiloxymethyl-N-(6-methylheptanoyl)serylamino]-6-methyl-1,2-oxiranylheptane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 82 percent / HBTU; Et₃N / CH₂Cl₂ / 8 h / 20 °C 2: 92 percent / imidazole / tetrahydrofuran / 24 h / 20 °C 3: 99 percent / H₂ / Pd-C / methanol / 2 h / 20 °C 4: 78 percent / HATU; i-Pr₂NEt / CH₂Cl₂ / 10 h / 20 °C

Reference： [1]Sin, Ny; Meng, Lihao; Auth, Hak; Crews, Craig M. [Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 8, p. 1209 - 1217]

16
[ 2270-59-9 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ethanol 2: potassium hydroxide / ethanol 3: hydrogen / platinum / ethanol

Reference： [1]Julia,S. et al. [Bulletin de la Societe Chimique de France, 1962, p. 1952 - 1959]

17
[ 24555-27-9 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol 2: hydrogen / platinum / ethanol

Reference： [1]Julia,S. et al. [Bulletin de la Societe Chimique de France, 1962, p. 1952 - 1959]

18
[ 1653-40-3 ]
[ 117692-89-4 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; titanium(IV) oxide In benzotrifluoride for 12h; Irradiation;

Reference： [1]Zhang, Miao; Wang, Qi; Chen, Chuncheng; Ma, Wanhong; Zhao, Jincai; Zang, Ling [Angewandte Chemie - International Edition, 2009, vol. 48, # 33, p. 6081 - 6084][Angewandte Chemie, 2009, vol. 121, # 33, p. 6197 - 6200]

19
C₄₈H₅₃NO₇ [ No CAS ]
[ 111-14-8 ]
[ 124-07-2 ]
[ 929-10-2 ]
[ 334-48-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₄₈H₅₃NO₇ With potassium permanganate; sodium periodate; potassium carbonate In <i>tert</i>-butyl alcohol at 37℃; for 18h; Stage #2: With sulfuric acid In <i>tert</i>-butyl alcohol	4.8.4. Microscale oxidation of sphinganine fraction D Compound 4 (100 μg) dissolved in 500 μL of 1 M HCl in 95% MeOH was incubated for 12 h at 80 °C in a sealed tube. The reaction mixture was dried under N2 flow and the resulting material was partitioned between CHCl3 (2 mL) and 20% MeOH (2 mL). Both layers were dried by N2 flow to deliver fraction A (from the 20% MeOH layer) and fraction B (from the CHCl3 layer). This process was also scaled to 1 mg of 4. The sample of fraction D (180 μg) was dissolved in t-BuOH (300 μL) and treated by the sequential addition of 40 mM K2CO3 (50 μL), 25 mM KMnO4 (200 μL) and 100 mM NaIO4 (200 μL). The mixture was warmed to 37 °C in a sealed vial. After 18 h, the mixture was acidified with 5 M H2SO4 and decolorized by the addition of a saturated solution of Na2SO3. The mixture was diluted with 1 mL of H2O and extracted with Et2O (3 × 5 mL). The combined extracts were dried with Na2SO4. The resulting solution was treated with 2 M TMSCHN2 in Et2O (500 μL) for 1 h at rt at which point it was concentrated to ∼200 μL by rotary evaporation. The resulting solution was evaluated by GC/MS. The results were as follows: methyl-heptanoate with tR = 2.5 min with M+ at m/z 144, methyl-6-methylheptanoate, tR = 3.6 min with M+ at m/z 158, methyl-octanoate, tR = 4.4 min with M+ at m/z 158. Relative abundances were determined by peak integration and were compared to a quantitative 1:1:1 mixture of methyl-heptanoate, methyl-6-methylheptanoate, and methyl-octanoate. These results are summarized in Figure 8.

Reference： [1]Location in patent: experimental part La Clair, James J.; Rodriguez, Abimael D. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 22, p. 6645 - 6653]

20
C₆₁H₁₀₇NO₁₉ [ No CAS ]
[ 111-14-8 ]
[ 124-07-2 ]
[ 929-10-2 ]
[ 334-48-5 ]
[ 112-37-8 ]
[ 2724-56-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₆₁H₁₀₇NO₁₉ With hydrogenchloride; methanol at 80℃; for 12h; Sealed tube; Stage #2: With potassium permanganate; sodium periodate; potassium carbonate In <i>tert</i>-butyl alcohol at 37℃; for 18h; Stage #3: With sulfuric acid In <i>tert</i>-butyl alcohol	4.8.5. Microscale oxidation of fraction B Compound 4 (100 μg) dissolved in 500 μL of 1 M HCl in 95% MeOH was incubated for 12 h at 80 °C in a sealed tube. The reaction mixture was dried under N2 flow and the resulting material was partitioned between CHCl3 (2 mL) and 20% MeOH (2 mL). Both layers were dried by N2 flow to deliver fraction A (from the 20% MeOH layer) and fraction B (from the CHCl3 layer). This process was also scaled to 1 mg of 4. Fraction B obtained from the methanolysis of 400 μg of 4 was dissolved in t-BuOH (150 μL) and treated by the sequential addition of 40 mM K2CO3 (25 μL), 25 mM KMnO4 (100 μL) and 100 mM NaIO4 (100 μL). The mixture was warmed to 37 °C in a sealed vial. After 18 h, the mixture was acidified with 5 M H2SO4 and decolorized by the addition of a saturated solution of Na2SO3. The mixture was diluted with 1 mL of H2O and extracted with Et2O (3 × 3 mL). The combined extracts were dried with Na2SO4. The resulting solution was treated with 2 M TMSCHN2 in Et2O (250 μL) for 1 h at rt at which point it was concentrated to ∼200 μL by rotary evaporation. The resulting solution was evaluated by GC/MS. The results were as follows: methyl-heptanoate with tR = 2.5 min and M+ at m/z 144, methyl-6-methylheptanoate, tR = 3.6 min, M+ at m/z 158, methyl-octanoate, tR = 4.4 min with M+ at m/z 158, methyl-decanoate, tR = 6.8 min with M+ at m/z 186, methyl-undecanoate, tR = 7.3 min with M+ at m/z 200, methyl-10-methylundecanoate, tR = 8.1 min with M+ at m/z 214 and methyl-dodecanoate with tR = 8.9 min, M+ at m/z 214. Relative abundances were determined by peak integration and were compared to a quantitative 1:1:1:1 mixture containing methyl-heptanoate, methyl-undecanoate, methyl-6-octanoate and methyl-dodecanoate. These results are summarized in Figure 8.

Reference： [1]Location in patent: experimental part La Clair, James J.; Rodriguez, Abimael D. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 22, p. 6645 - 6653]

21
[ 929-10-2 ]
[ 84500-43-6 ]
[ 1647153-61-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dmap; diisopropyl-carbodiimide In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	(2S,3S)-N-(Benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester (28) DIC (10 μL, 65 μmol, 2.4 equiv) was added at room temperature to a solution of 24 (10 mg, 27 μmol, 1.0 equiv), 6-methylheptanoic acid (26, 6.0 mg, 42 μmol, 1.5 equiv) and DMAP (8.0 mg, 66 μmol, 2.4 equiv) in dry THF (1 mL) under argon atmosphere and stirred for 16 h at this temperature. The reaction mixture was then acidified with hydrochloric acid (0.5 M, 5 mL) and the aqueous layer was extracted with CH2Cl2 (3 × 5 mL). The combined organics were dried over Na2SO4 and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (SiO2, petroleum ether/EtOAc 4:1) yielding 13 mg (25 μmol, 94%) of 28 as a clear oil. TLC Rf 0.39 (petroleum ether/EtOAc 4:1); 1H NMR (300 MHz, CDCl3): 0.84 (d, 6H, J = 6.6 Hz, 7'-H3, 7'-H3), 0.87 (d, 3H, J = 6.7 Hz, 5-H3), 0.99 (d, 3H, J = 6.7 Hz, 5-H3), 1.06-1.31 (m, 4H, 4'-H2, 5'-H2), 1.40-1.59 (m, 3H, 3'-H2, 6'-H), 1.97-2.24 (m, 3H, 4-H, 2'-H2), 4.69 (dd, 1H, J = 8.5, 3.4 Hz, 2-H), 4.82 (dd, 1H, J = 8.3, 3.4 Hz, 3-H), 5.09 (s, 2H, NCO2CH2Ph), 5.16 (s, 2H, CO2CH2Ph), 5.63 (d, 1H, J = 8.5 Hz, NH), 7.22-7.42 (m, 10H, Ph-H); 13C NMR (126 MHz, CDCl3): 18.5, 19.3, 22.6, 22.6, 25.1, 27.0, 27.9, 29.4, 34.2, 38.6, 55.7, 67.1, 67.4, 79.0, 128.0, 128.1, 128.3, 128.4, 128.4, 128.5, 135.0, 136.1, 155.5, 169.1, 173.5; IR (ATR) ν 2954, 1724, 1499, 1215, 1163, 1002, 735, 695; UV (MeCN) λmax (log ε) 206 (4.20), 258 (2.91); [α]D20 -12.2 (c 12.4, MeOH); MS (ESI+) m/z 520.3 (M+Na+); HRMS (ESI+) m/z calcd for C29H39NNaO6 520.2670 (M+Na+), found 520.2663.

Reference： [1]Ries, Oliver; Bueschleb, Martin; Granitzka, Markus; Stalke, Dietmar; Ducho, Christian [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1135 - 1142]

22
benzyl 6-methylhept-2-enoate [ No CAS ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol at 20℃; for 5h; Inert atmosphere;	6-Methylheptanoic acid (26) A solution of 33 (189 mg, 0.814 mmol, 1.0 equiv) in MeOH (10 mL) was degassed with a stream of argon and subsequently treated with Pearlman's catalyst (114 mg, 81.5 μmol, 0.1 equiv). The reaction mixture was stirred for 5 h under hydrogen atmosphere (1 bar, balloon) at room temperature and then filtered through a SPARTAN syringe filter. The solvent of the filtrate was removed under reduced pressure and the resultant residue was dissolved in a small amount of EtOAc and dried over Na2SO4. The solvent was removedS18under reduced pressure yielding 107 mg (0.742 mmol, 92%) of 26 as a clear liquid which was used without further purification. 1H NMR (300 MHz, CDCl3): 0.85 (d, 6H, J = 6.6 Hz, 7-H3, 7-H3), 1.11-1.22 (m, 2H, 5-H2), 1.24-1.38 (m, 2H, 4-H2), 1.52 (qqt, 1H, J = 6.6, 6.6, 6.6 Hz, 6-H), 1.60 (tt, 2H, J = 7.5, 7.5 Hz, 3-H2), 2.33 (t, 2H, J = 7.5 Hz, 2-H2); 13C NMR (75 MHz, CDCl3): 22.5, 24.9, 26.8, 27.8, 34.1, 38.5, 180.4; IR (ATR) ν 2953, 1707, 1466, 1412, 1286, 1238, 1166, 1113, 935; MS (ESI-) m/z 143.1 (M-H+); HRMS (ESI-) m/z calcd for C8H15O2 143.1078 (M-H+), found 143.1076.

Reference： [1]Ries, Oliver; Bueschleb, Martin; Granitzka, Markus; Stalke, Dietmar; Ducho, Christian [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1135 - 1142]

23
(2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid [ No CAS ]
[ 929-10-2 ]
[ 35661-60-0 ]
[ 71989-35-0 ]
[ 86123-10-6 ]
[ 125238-99-5 ]
[ 688316-86-1 ]
6-methylheptanoyl-X-T-X-cyclo[X-X-DF-L-X-X-T] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		General procedure: 2CTC resin (0.47g,loading = 0.53mmol/g ) was swelled in DCM/DMF for 20min before use. Then,Fmoc-Dab-OAll (1mmol, 4 eq), 8 eq. DIEA and 4ml DMF were added to react withresin for 12hr. The resin was capped with 200 mlmethanol to quench the remaining 2-chlorotrityl chloride. Generally, thesubsequent coupling was carried out using a solution of 4 eq. Fmoc-amino acid,3.8 eq. HCTU, and 8 eq. DIEA in DMF at 30 oC. Each coupling steprequired 1hr and the resin was washed by DMF and DCM before Fmoc-deprotection. The Fmoc group wasremoved by treatment with 20% piperidine in DMF twice (5 min, 10 min) followedby DMF and DCM wash. Dde group wasremoved by treatment with 3% NH2NH2/DMF for 20min threetimes. Allyl group wasremoved by treatment with PhSiH3 (10 eq.), Pd(PPh3)4(2 eq.) in 50% DCM/50% DMF for 3 hrs. After deprotection, the resin waswashed with DCM, 0.5% sodium diethyldithiocarbamate in DMF and DMF severaltimes. The finalcyclization step was carried out with 4 eq. PyAOP, 4eq. HOAt and 8eq.NMM for12hr. The cleavage reagentwas chose as TFA/water/TIPS (95/2.5/2.5). It was added into the dry resinprewashed with DCM and the cleavage was carried out for 1.5 hr. The TFAsolution was concentrated by blowing with N2. The crude peptideswere obtained by precipitating with cold diethyl ether, purified bysemi-preparative HPLC and lyophilized to achieve pure product.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4796 - 4799

24
(2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid [ No CAS ]
[ 929-10-2 ]
[ 35661-60-0 ]
[ 71989-35-0 ]
[ 35661-60-0 ]
[ 125238-99-5 ]
[ 688316-86-1 ]
polymyxin E₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		General procedure: 2CTC resin (0.47g,loading = 0.53mmol/g ) was swelled in DCM/DMF for 20min before use. Then,Fmoc-Dab-OAll (1mmol, 4 eq), 8 eq. DIEA and 4ml DMF were added to react withresin for 12hr. The resin was capped with 200 mlmethanol to quench the remaining 2-chlorotrityl chloride. Generally, thesubsequent coupling was carried out using a solution of 4 eq. Fmoc-amino acid,3.8 eq. HCTU, and 8 eq. DIEA in DMF at 30 oC. Each coupling steprequired 1hr and the resin was washed by DMF and DCM before Fmoc-deprotection. The Fmoc group wasremoved by treatment with 20% piperidine in DMF twice (5 min, 10 min) followedby DMF and DCM wash. Dde group wasremoved by treatment with 3% NH2NH2/DMF for 20min threetimes. Allyl group wasremoved by treatment with PhSiH3 (10 eq.), Pd(PPh3)4(2 eq.) in 50% DCM/50% DMF for 3 hrs. After deprotection, the resin waswashed with DCM, 0.5% sodium diethyldithiocarbamate in DMF and DMF severaltimes. The finalcyclization step was carried out with 4 eq. PyAOP, 4eq. HOAt and 8eq.NMM for12hr. The cleavage reagentwas chose as TFA/water/TIPS (95/2.5/2.5). It was added into the dry resinprewashed with DCM and the cleavage was carried out for 1.5 hr. The TFAsolution was concentrated by blowing with N2. The crude peptideswere obtained by precipitating with cold diethyl ether, purified bysemi-preparative HPLC and lyophilized to achieve pure product.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4796 - 4799

25
[ 929-10-2 ]
[ 112-27-6 ]
triethylene glycol di-iso-octanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis((1,1,1-trifluoro-N-(trifluoromethyl)sulfonyl)methylsulfonamido)zinc; boron trifluoride diethyl etherate; tin(II) oxide at 220℃; for 5h;	1 Example 3 The 100 kg triethylene glycol, 480 kg to isooctoate 1000L reactor, is added to the reactor the catalyst prepared in the above-mentioned step 29 kg, the reaction temperature is 250 °C, reaction 3 hours, tri-glycerinate get crude reaction is ended mellow two different caprylate, tri-glycerinate the mellow two different caprylate crude product by washing, distillation purification, remove redundant unhydride, ester triethylene glycol two different bitter obtain the final product. Numbered M-3.

Reference： [1]Current Patent Assignee: SHENYANG ZHANGMING CHEMICAL - CN105439850, 2016, A Location in patent: Paragraph 0032; 0033

26
[ 929-10-2 ]
[ 115-11-7 ]
tert-butyl 6-methylheptanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With mesophorous Al-SBA-15-SO₃H catalyst at 10℃; for 20h; Autoclave;	8 Example 8 In a 300 mL autoclave72.10 g of isooctanoic acid was chargedAnd 21.63 g of mesoporous Al-SBA-15-SO3H having an Al doping amount of 1% and a sulfonic acid group loading of 30% prepared in the one-step co-condensation method in Example 1,After 168.00 g of isobutene was passed thereinto, the mixture was heated to 10 ° C,And the reaction was carried out for 20 h at a stirring speed of 400 r / min.The reaction solution was centrifuged to remove the catalyst,The liquid phase was analyzed by gas chromatography,The analysis results showed that the conversion of isooctanoic acid was 92.2%The selectivity of tert-butyl isooctanoate was 95.2%Diisobutene selectivity was 4.8% (selectivity are based on isobutylene basis, the same below).

Reference： [1]Current Patent Assignee: NANJING TOP CHEMICAL; NANJING UNIVERSITY - CN103936583, 2016, B Location in patent: Paragraph 0038; 0039

27
potassium isooctanoate [ No CAS ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
98.1%	With formic acid In water at 40℃; for 0.5h; Large scale;	7 Example 7 The aqueous potassium isooctanoate solution was transferred to a neutralization kettle,2070 kg of a 94 wt% formic acid solution was slowly added with stirring,The reaction temperature was controlled at 40 ° C,Reaction 30min,Moved to the separation kettle,Standing for 30min,The aqueous phase was separated by layering,The aqueous phase is potassium formate solution;The oil phase was washed twice with 600 kg of distilled water to give crude isooctanoic acid,The unreacted alcohol was distilled off under reduced pressure,Distillation of isooctanoic acid products 5428kg,The yield was 108.56% by weight of isooctyl alcohol,The molar yield was 98.1%.

Reference： [1]Current Patent Assignee: TAIAN HAVAY CHEMICALS - CN106278875, 2017, A Location in patent: Paragraph 0041; 0043

28
[ 874743-11-0 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
98.14%	With chloroacetic acid In water at 40℃; for 0.5h; Large scale;	6 Example 6 The aqueous sodium isooctanoate solution was transferred to a neutralization kettle,And 10,300 kg of a 50 wt% solution of chloroacetic acid was slowly added with stirring,The reaction temperature was controlled at 40 ° C,Reaction 30min,Moved to the separation kettle,Standing for 30min,The aqueous phase was separated by layering,The aqueous phase is sodium chloroacetate solution;The oil phase was washed twice with 600 kg of distilled water to give crude isooctanoic acid,The unreacted alcohol was distilled off under reduced pressure,Distillation of isooctanoic acid products 5432kg,The yield was 108.64% by weight of isooctanol,The molar yield was 98.14%.

Reference： [1]Current Patent Assignee: TAIAN HAVAY CHEMICALS - CN106278875, 2017, A Location in patent: Paragraph 0038; 0040

29
[ 929-10-2 ]
[ 106-76-3 ]
[ 753-73-1 ]
C₂₀H₄₀O₄SSn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: isooctyl mercaptoacetate; dimethyltin dichloride With ammonia In water at 50℃; for 0.833333h; Stage #2: isooctanoic acid With sodium hydroxide In water for 2h;	1 Example 1 In a three-necked flask equipped with a thermometer and a stirrer, 100 g of an aqueous dichlorodimethyltin solution,51 g of isooctyl mercaptoacetate were mixed,Stirring,Heated to 50 ° C,7.1 g of aqueous ammonia (30 wt%) was slowly added dropwise,After dropping off, close the separatory funnel,Reaction for 50 minutes,Further, 35.7 g of isooctanoic acid,Sodium hydroxide (12 wt%) was slowly added dropwise to the aqueous phase pH & gt; 6.5,The reaction was carried out for 60 minutes,Standing for 1 hour,Layered,Take oil phase dehydration,filter,To obtain a mixed anion-methyl-1 tin,After analysis,The tin content was 22.4%.

Reference： [1]Current Patent Assignee: ZHEJIANG HIMPTON NEW MATERIAL CO LTD - CN106279249, 2017, A Location in patent: Paragraph 0028; 0029

30
[ 77-99-6 ]
[ 929-10-2 ]
C₃₀H₅₆O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With chlorosulfonic acid; 3,5-dichloro-2-hydroxybenzenesulfonyl chloride; 3-methylimidazoletrifluoromethanesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; propan-1-ol; at 200℃; for 10h;Large scale;	(1) In a 2000 L autoclave, 100 kg of cross-linked polystyrene polymer white ball, 400 kg of tetrahydrofuran,20Kg3,5-dichloro-2-hydroxybenzenesulfonyl chloride, and the mixture was stirred at 80 C for 10 hours to filter out a resin having a sulfonyl group.(2) 100 kg of a resin having a sulfonyl group, 400 Kg of chlorosulfonic acid, 0.5 Kg of 1-propane3-methylimidazole trifluoromethanesulfonate, reacted at 80 C for 1 h, filtered, and then 50 Kg of p-toluenesulfonic acid was added thereto.80 reaction 1h, the end of the reaction, filtration, obtained composite catalyst, spare;(3) Synthesis reaction:Trimethylolpropane, isooctanoic acid into the reactor, the catalyst prepared in the above step is added to the reactor,The molar ratio of <strong>[77-99-6]trimethylolpropane</strong> to isooctanoic acid is 1: 5, the amount of catalyst is <strong>[77-99-6]trimethylolpropane</strong> and isooctanoic acid15%, reaction temperature 200 , reaction 10 hours, the end of the reaction to get crude trimethylol propane triisooctanoate, crude trihydroxyMethylpropane triisooctanoate is washed, distilled and purified to remove excess isooctanoic acid to give the final product <strong>[77-99-6]trimethylolpropane</strong>Triisooctanoate. No. M-3.

Reference： [1]Patent: CN106397192,2017,A .Location in patent: Paragraph 0021; 0022; 0023; 0024; 0025; 0026; 0027-0047

31
tin(II) hydroxide [ No CAS ]
[ 929-10-2 ]
C₁₆H₃₀O₄Sn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With C₇H₁₂N₂O₄ at 160℃; for 5h;	3.2 Example 3 (2) The isooctanoic acid and the stannous hydroxide powder were mixed at 2: 1 (molar ratio), 3 ‰ catalyst was added (R7 was ethyl group, R8 is amino group)), and the temperature was raised to 160 ° C. The reaction was carried out for 5 hours, After the end of the reaction, the crude product of the organotin compound is cooled and the crude of the organotin compound is cooled to 40 ° C to obtain the finished product of the organotin compound, and the conversion is 99.9% in terms of stannous hydroxide.

Reference： [1]Current Patent Assignee: JIANGSU FEITUO INTERFACE ENG TECH - CN106083913, 2016, A Location in patent: Paragraph 0014

32
N-α-(9-fluorenylmethoxycaebonyl)-N-γ-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl]-L-2,4-diaminobutyric acid [ No CAS ]
[ 929-10-2 ]
Fmoc-Thr(OtBu)-O-Pol [ No CAS ]
[ 71989-35-0 ]
[ 35661-60-0 ]
[ 73724-45-5 ]
[ 125238-99-5 ]
C₈₁H₁₄₉N₁₅O₂₄ [ No CAS ]

Reference： [1]Journal of Natural Products,2017,vol. 80,p. 1264 - 1274

33
[ 3859-30-1 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-Bromosuccinimide; perchloric acid / 1,4-dioxane 2: potassium hydroxide 3: hydrogen / platinum / ethanol

Reference： [1]Julia,S. et al. [Bulletin de la Societe Chimique de France, 1962, p. 1952 - 1959]

34
[ 5212-66-8 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide 2: hydrogen / platinum / ethanol

Reference： [1]Julia,S. et al. [Bulletin de la Societe Chimique de France, 1962, p. 1952 - 1959]

35
[ 120-92-3 ]
[ 929-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 2: N-Bromosuccinimide; perchloric acid / 1,4-dioxane 3: potassium hydroxide 4: hydrogen / platinum / ethanol

Reference： [1]Julia,S. et al. [Bulletin de la Societe Chimique de France, 1962, p. 1952 - 1959]

36
[ 929-10-2 ]
[ 105-08-8 ]
1,4-cyclohexanedimethanol diisooctanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With SO₄^(2-)/TiO₂/Ce at 150℃; for 10h;	1.2.1 Step 2. Synthesis of 1,4-cyclohexanedimethanol diisooctanoate. Add 1 ,4-cyclohexanedimethanol and isooctanoic acid prepared in Step 1 to the reaction vessel, then add the super acid catalyst SO42-/TiO2/Ce, reaction temperature 150 °C, reaction for 10 h, and stop the heating after the reaction is completed. Crude. Step 3: Post-processing of the product. The reaction solution was filtered, and the catalyst was filtered, washed, dried, and reused. The filtrate was washed 4 times with 5% NaOH solution. The organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, and distilled under a reduced pressure to give a slightly yellow oily liquid.

Reference： [1]Current Patent Assignee: PANJIN HONGDING CHEMICAL - CN107778175, 2018, A Location in patent: Paragraph 0028-0030; 0037

37
[ 929-10-2 ]
Fmoc-L-Dab(Dde)-OH, DDE = 1-(4,4-dimethyl-2,6-dioxocylohexylidene)ethyl [ No CAS ]
[ 71989-35-0 ]
[ 86123-10-6 ]
[ 125238-99-5 ]
[ 76-05-1 ]
[ 688316-86-1 ]
Fmoc-D-Ser(pg)-OH [ No CAS ]
polymyxin S₂ TFA salt [ No CAS ]