Production Method 1

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Sodium iodide Solvents: Acetone ;  25 h, rt

Reference

Toward intrinsically colored peptides: Synthesis and investigation of the spectral properties of methylated azatryptophans in tryptophan-cage mutants

Noichl, Benjamin P.; Durkin, Patrick M.; Budisa, Nediljko, Biopolymers, 2015, 104(5), 585-600

Production Method 2

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dimethylformamide ;  3 h, 0 °C → rt

Reference

Application of bis-2-(trimethylsilyl)ethyl diselenide to the synthesis of selenium-containing amino acid derivatives

Yonezawa, Tsubasa; Yamaguchi, Masahito; Ninomiya, Masayuki; Koketsu, Mamoru, Tetrahedron, 2017, 73(42), 6085-6091

Production Method 3

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  0 °C; 0 °C → rt; 10 min, rt; rt → 0 °C
1.2 Solvents: Dichloromethane ;  0 °C; 1 h, 0 °C; 1.5 h, rt

Reference

Synthesis of disulfides and diselenides by copper-catalyzed coupling reactions in water

Li, Zhengkai; Ke, Fang; Deng, Hang; Xu, Hualong; Xiang, Haifeng; et al, Organic & Biomolecular Chemistry, 2013, 11(18), 2943-2946

Production Method 4

56926-94-4

93267-04-0

Reaction Conditions

1.1 Reagents: Sodium iodide Solvents: Acetone ;  30 min, 10 - 30 °C; 21.5 h, 20 - 30 °C

Reference

Synthesis of 4-chlorokynurenines and intermediates

, World Intellectual Property Organization, , ,

Production Method 5

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine Solvents: Dichloromethane ;  10 min, rt; rt → 0 °C
1.2 Reagents: Iodine ;  20 min, 0 - 7 °C; 7 °C → rt; 10 min, rt; rt → 0 °C
1.3 Solvents: Dichloromethane ;  60 min, 0 °C; 1 h, 0 °C; 1 h, 0 °C → rt; 1.5 h, rt

Reference

Preparation of N-(Boc)-allylglycine methyl ester using a zinc-mediated, palladium-catalyzed cross-coupling reaction

Prasad Atmuri, N. D.; Lubell, William D., Organic Syntheses, 2015, 92, 103-116

Production Method 6

56926-94-4

93267-04-0

Reaction Conditions

1.1 Reagents: Sodium iodide Solvents: Acetone ;  3 d, rt; 1 d, rt

Reference

Synthesis of N-(tert-butoxycarbonyl)-β-iodoalanine methyl ester: A useful building block in the synthesis of nonnatural α-amino acids via palladium catalyzed cross coupling reactions

Jackson, Richard F. W.; Perez-Gonzalez, Manuel, Organic Syntheses, 2005, 81, 77-88

Production Method 7

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  0 °C; 10 min, 0 °C; 15 min, rt
1.2 Solvents: Dichloromethane ;  0 °C; 4 h, rt
1.3 Reagents: Sodium thiosulfate Solvents: Water ;  rt

Reference

Alkyl Carbagermatranes Enable Practical Palladium-Catalyzed sp2-sp3 Cross-Coupling

Xu, Meng-Yu; Jiang, Wei-Tao; Li, Ying; Xu, Qing-Hao; Zhou, Qiao-Lan; et al, Journal of the American Chemical Society, 2019, 141(18), 7582-7588

Production Method 8

56926-94-4

93267-04-0

Reaction Conditions

1.1 Reagents: Sodium iodide Solvents: Acetone ;  24 h, rt

Reference

Synthesis of N-Boc-3-iodo-zinc-L-alanine methyl ester

Huang, Suo-yi; Wang, Lin-sheng, Huagong Jishu Yu Kaifa, 2004, 33(2), 13-16

Production Method 9

3262-72-4

93267-04-0

Reaction Conditions

1.1 Reagents: Potassium bicarbonate Solvents: Dimethylformamide
1.2 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  0 °C; 10 min, 0 °C → rt; rt → 0 °C
1.3 3.5 h, 0 °C
1.4 Reagents: Sodium thiosulfate Solvents: Water

Reference

Readily available amino acid building blocks for the synthesis of phosphole-containing peptides

van Zutphen, Steven; Margarit, Vicente J.; Mora, Guilhem; Le Floch, Pascal, Tetrahedron Letters, 2007, 48(16), 2857-2859

Production Method 10

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 2.5 h, rt

Reference

The silica mineralisation properties of synthetic Silaffin-1A1 (synSil-1A1)

Daus, Fabian; Xie, Xiulan; Geyer, Armin, Organic & Biomolecular Chemistry, 2022, 20(16), 3387-3396

Production Method 11

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane

Reference

Synthesis of conformationally restricted Beta-turn mimics

Ijsselstijn, Maarten, 2006, , ,

Production Method 12

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  5 min, rt
1.2 Solvents: Dichloromethane ;  2 h, rt

Reference

Thiomaleic Anhydride: A Convenient Building Block for the Synthesis of α-Substituted γ- and δ-Lactones through Free-Radical Addition, Nucleophilic Ring Opening, and Subsequent Thiocarboxylate Manipulation

Crich, David; Rahaman, Yeajur Md., Journal of Organic Chemistry, 2009, 74(17), 6792-6796

Production Method 13

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  0 °C; 5 min, 0 °C; 10 min, rt; rt → 0 °C
1.2 Solvents: Dichloromethane ;  10 min, 0 °C; 90 min, 0 °C

Reference

Painting argyrins blue: Negishi cross-coupling for synthesis of deep-blue tryptophan analog β-(1-azulenyl)-L-alanine and its incorporation into argyrin C

Stempel, Erik; Kaml, Robert Franz-Xaver; Budisa, Nediljko; Kalesse, Markus, Bioorganic & Medicinal Chemistry, 2018, 26(19), 5259-5269

Production Method 14

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  0 °C; 10 min, rt; rt → 0 °C
1.2 Solvents: Dichloromethane ;  30 min, 0 °C; 1 h, 0 °C; 1.5 h, rt

Reference

Use of a Tandem Prins/Friedel-Crafts Reaction in the Construction of the Indeno-Tetrahydropyridine Core of the Haouamine Alkaloids: Formal Synthesis of (-)-Haouamine A

Fenster, Erik; Fehl, Charlie; Aube, Jeffrey, Organic Letters, 2011, 13(10), 2614-2617

Production Method 15

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  1 h, 0 °C; 1.5 h, rt

Reference

Chemoselectivity of the Ruthenium-Catalyzed Hydrative Diyne Cyclization: Total Synthesis of (+)-Cylindricine C, D, and E

Trost, Barry M.; Rudd, Michael T., Organic Letters, 2003, 5(24), 4599-4602

Production Method 16

56926-94-4

93267-04-0

Reaction Conditions

1.1 Reagents: Sodium iodide Solvents: Acetone ;  rt; 42 h, rt

Reference

Preparation of cyclopentylcarbonylamino acid as inhibitors of α4β1 mediated cell adhesion

, World Intellectual Property Organization, , ,

Production Method 17

2766-43-0

93267-04-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  0 °C; 10 min, rt; rt → 0 °C
1.2 Solvents: Dichloromethane ;  0 °C; 2 h, 0 °C

Reference

Synthesis and applications of highly functionalized 1-halo-3-substituted bicyclo[1.1.1]pentanes

Caputo, Dimitri F. J.; Arroniz, Carlos; Durr, Alexander B.; Mousseau, James J.; Stepan, Antonia F.; et al, Chemical Science, 2018, 9(23), 5295-5300

Production Method 18

187035-34-3

93267-04-0

Reaction Conditions

1.1 Reagents: Sodium iodide Solvents: Acetone

Reference

Synthesis of all three regioisomers of pyridylalanine

Walker, Michael A.; Kaplita, Khane Pham; Chen, Ti; King, Dalton H., Synlett, 1997, (2), 169-170

Production Method 19

56926-94-4

93267-04-0

Reaction Conditions

1.1 Reagents: Iodine Solvents: Acetone

Reference

Organocuprates in a novel synthesis of optically pure amino acids

Bajgrowicz, J. A.; El Hallaoui, A.; Jacquier, R.; Pigiere, C.; Viallefont, P., Tetrahedron, 1985, 41(10), 1833-43

Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate Raw materials

• (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxypropanoic acid
• S-methyl 2-((tert-butoxycarbonyl)amino)-3-((methylsulfonyl)oxy)propanoate
• Boc-Ser-OMe
• Boc-Ser(Tos)-OMe

Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate Preparation Products

• Methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropanoate (93267-04-0)

• 1. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210
• 2. An insight into the origin of room-temperature ferromagnetism in SnO2 and Mn-doped SnO2 quantum dots: an experimental and DFT approach?
  Dhamodaran Manikandan,S. Amirthapandian,I. S. Zhidkov,A. I. Kukharenko,S. O. Cholakh,Ramaswamy Murugan Phys. Chem. Chem. Phys., 2018,20, 6500-6514
• 3. An insight into the role of side chains in the microstructure and carrier mobility of high-performance conjugated polymers?
  Jianyao Huang,Dong Gao,Zhihui Chen,Weifeng Zhang Polym. Chem., 2021,12, 2471-2480
• 4. An amorphous carbon nitride/NiO/CoN-based composite: a highly efficient nonprecious electrode for supercapacitors and the oxygen evolution reaction?
  Huifang Yang,Haoran Guo,Peidong Fan,Xinpan Li,Wenlu Ren,Rui Song Nanoscale, 2020,12, 7024-7034
• 5. Achieving excellent anti-corrosion and tribological performance by tailoring the surface morphology and chemical composition of aluminum alloys
  Wenjie Zhao,Hua Hou,Yuchun Jin,Zhixiang Zeng,Xuedong Wu,Qunji Xue RSC Adv., 2014,4, 60307-60315

• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 125942-79-2(boc-3-iodo-d-alanine benzyl ester)
• 850630-45-4(D-ALANINE, 3-IODO-N-[(2-PROPENYLOXY)CARBONYL]-, 2-PROPENYL ESTER)
• 91103-47-8(Boc-D-Ala-OMe)
• 112392-66-2(Alanine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester)
• 51814-53-0(L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-, ethyl ester)
• 170848-34-7((S)-2-[(tert-Butoxycarbonyl)amino]-3-iodopropionic acid methyl ester)
• 28875-17-4(Boc-Ala-OMe)
• 58177-77-8(N-(tert-Butoxycarbonyl)alanine tert-Butyl Ester)
• 889670-02-4(Methyl 2-(tert-Butoxycarbonylamino)-3-iodopropanoate)
• 108728-93-4(L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-, iodomethyl ester)