Production Method 1

356048-04-9

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water
1.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol

Reference

Enantioselective synthesis of (S)- and (R)-α-methylserines: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals

Avenoza, A.; et al, Tetrahedron: Asymmetry, 2001, 12(6), 949-957

Production Method 2

81132-44-7

Reaction Conditions

Reference

Product subclass 7: 2-aminoalkanoic acids (α-amino acids)

Wolkenberg, S. E.; et al, Science of Synthesis, 2006, 20, 385-482

Production Method 3

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  4 h, 90 °C
1.2 Reagents: (±)-Propylene oxide Solvents: Ethanol ;  30 min, rt

Reference

A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones

Wang, Hai-Fei; et al, Tetrahedron: Asymmetry, 2008, 19(13), 1630-1635

Production Method 4

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol ,  Water

Reference

Preparative asymmetric synthesis of (R)- and (S)-α-methylserine via nickel(II) complex with the Schiff base of α-alanine and (S)-2-[(N-benzylprolyl)amino]benzophenone

Belokon, Yu. N.; et al, Izvestiya Akademii Nauk SSSR, 1991, (5), 1175-80

Production Method 5

445283-77-2

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ;  5 d, 70 psi, rt
1.2 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  1 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt

Reference

Stereoselective addition of organometallic reagents to a chiral acyclic nitrone derived from L-erythrulose

Murga, Juan; et al, Tetrahedron: Asymmetry, 2005, 16(10), 1807-1816

Production Method 6

188909-49-1

81132-44-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol

Reference

Stereoselective synthesis of α-substituted serines from protected erythrulose oximes

Carda, M.; et al, Tetrahedron: Asymmetry, 1998, 9(10), 1703-1712

Production Method 7

132839-93-1

81132-44-7

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran
1.2 Reagents: Acetic anhydride Solvents: Water

Reference

Completely regioselective hydroformylation of methyl N-acetamidoacrylate by chiral rhodium phosphine catalysts

Gladiali, Serafino; et al, Tetrahedron: Asymmetry, 1990, 1(10), 693-6

Production Method 8

81132-44-7

Reaction Conditions

Reference

Product subclass 7: 2-aminoalkanoic acids (α-amino acids)

Wolkenberg, S. E.; et al, Science of Synthesis, 2006, 20, 385-482

Production Method 9

81132-44-7

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  10 min, -78 °C; 30 min, -78 °C
1.2 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
1.3 Solvents: Tetrahydrofuran ;  10 min, -78 °C; 2 h, -78 °C
1.4 Reagents: Ammonium chloride Solvents: Water ;  -78 °C → rt
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  4 h, 90 °C
2.2 Reagents: (±)-Propylene oxide Solvents: Ethanol ;  30 min, rt

Reference

A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones

Wang, Hai-Fei; et al, Tetrahedron: Asymmetry, 2008, 19(13), 1630-1635

Production Method 10

81132-44-7

Reaction Conditions

1.1 Reagents: Sodium methoxide Solvents: Methanol
2.1 Reagents: Hydrochloric acid Solvents: Methanol ,  Water

Reference

Preparative asymmetric synthesis of (R)- and (S)-α-methylserine via nickel(II) complex with the Schiff base of α-alanine and (S)-2-[(N-benzylprolyl)amino]benzophenone

Belokon, Yu. N.; et al, Izvestiya Akademii Nauk SSSR, 1991, (5), 1175-80

Production Method 11

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  rt; 21 h, reflux
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  3.5 h, rt

Reference

Chemoenzymatic synthesis of α-substituted serines via enantiodivergent transformation

Sano, Shigeki; et al, Open Organic Chemistry Journal, 2009, 3, 22-34

Production Method 12

188909-47-9

81132-44-7

Reaction Conditions

1.1 Reagents: p-Toluenesulfonic acid ,  1,2-Ethanedithiol Solvents: Chloroform
1.2 Reagents: Sodium periodate Solvents: Tetrahydrofuran ,  Water
1.3 Reagents: Sodium chlorite Solvents: tert-Butanol ,  Water
1.4 -
2.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water
2.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol

Reference

Diastereoselective additions of organolithium reagents to the C=N bond of protected erythrulose oxime ethers. Synthesis of enantiopure α,α-disubstituted α-amino acids

Marco, J. Alberto; et al, Tetrahedron Letters, 1997, 38(10), 1841-1844

Production Method 13

113312-55-3

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  3.5 h, rt

Reference

Chemoenzymatic synthesis of α-substituted serines via enantiodivergent transformation

Sano, Shigeki; et al, Open Organic Chemistry Journal, 2009, 3, 22-34

Production Method 14

356048-04-9

81132-44-7

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Methanol ,  Water ;  10 min, rt
1.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  overnight, rt

Reference

Enantioselective Synthesis of α-Methyl-D-cysteine and Lanthionine Building Blocks via α-Methyl-D-serine-β-lactone

Smith, Nicole D.; et al, Organic Letters, 2003, 5(7), 1035-1037

Production Method 15

81132-44-7

Reaction Conditions

1.1 Reagents: Ozone Solvents: Ethyl acetate
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Novel and efficient transformation of α-amino nitriles to α-imino and α-amido nitriles in asymmetric Strecker synthesis

Namba, K.; et al, Tetrahedron Letters, 2001, 42(22), 3733-3736

Production Method 16

81132-44-7

Reaction Conditions

1.1 Reagents: Triethylamine ,  tert-Butyl hypochlorite
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Asymmetric synthesis of α,α-disubstituted α-amino acids

Ohfune, Yasufumi; et al, Pure and Applied Chemistry, 1996, 68(3), 645-648

Production Method 17

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  6 h, 90 °C
1.2 Reagents: (±)-Propylene oxide Solvents: Ethanol ;  30 min, rt

Reference

A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones

Wang, Hai-Fei; et al, Tetrahedron: Asymmetry, 2008, 19(13), 1630-1635

Production Method 18

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol ,  Water
1.2 Reagents: Ammonium hydroxide Solvents: Water

Reference

Asymmetric synthesis of (S)- and (R)-α-methylserine based on the chiral recyclable reagent (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Belokon', Yu. N.; et al, Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, 2001, 50(6), 1037-1040

Production Method 19

445283-77-2

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide
1.2 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water

Reference

Synthesis of α,α-disubstituted α-amino acid derivatives in enantiopure form via stereoselective addition of Grignard reagents to a chiral acyclic nitrone derived from L-erythrulose

Portoles, Raul; et al, Synlett, 2002, (5), 711-714

Production Method 20

188909-51-5

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol

Reference

Stereoselective synthesis of α-substituted serines from protected erythrulose oximes

Carda, M.; et al, Tetrahedron: Asymmetry, 1998, 9(10), 1703-1712

Production Method 21

188909-49-1

81132-44-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water
1.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol

Reference

Diastereoselective additions of organolithium reagents to the C=N bond of protected erythrulose oxime ethers. Synthesis of enantiopure α,α-disubstituted α-amino acids

Marco, J. Alberto; et al, Tetrahedron Letters, 1997, 38(10), 1841-1844

Production Method 22

81132-44-7

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  10 min, -78 °C; 30 min, -78 °C
1.2 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
1.3 Solvents: Tetrahydrofuran ;  10 min, -78 °C; 2 h, -78 °C
1.4 Reagents: Ammonium chloride Solvents: Water ;  -78 °C → rt
2.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  6 h, 90 °C
2.2 Reagents: (±)-Propylene oxide Solvents: Ethanol ;  30 min, rt

Reference

A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones

Wang, Hai-Fei; et al, Tetrahedron: Asymmetry, 2008, 19(13), 1630-1635

Production Method 23

81132-44-7

Reaction Conditions

1.1 Solvents: Isopropanol
2.1 Reagents: Triethylamine ,  tert-Butyl hypochlorite
2.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Asymmetric synthesis of α,α-disubstituted α-amino acids

Ohfune, Yasufumi; et al, Pure and Applied Chemistry, 1996, 68(3), 645-648

Production Method 24

35356-70-8

81132-44-7

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Carbonylhydridotris(triphenylphosphine)rhodium ,  (-)-DIOP Solvents: Methyl ethyl ketone
2.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran
2.2 Reagents: Acetic anhydride Solvents: Water

Reference

Completely regioselective hydroformylation of methyl N-acetamidoacrylate by chiral rhodium phosphine catalysts

Gladiali, Serafino; et al, Tetrahedron: Asymmetry, 1990, 1(10), 693-6

a-Methyl-D-serine Raw materials

• methyl 2-acetamidoprop-2-enoate
• D-Alanine, N-acetyl-2-methyl-3-oxo-, methyl ester
• (2R)-2-Azido-3-hydroxy-2-methyl-propanoic Acid Methyl Ester
• (R)-2-(benzyloxycarbonylamino)-3-hydroxy-2-methylpropanoic acid
• D-Serine, 2-methyl-N-(phenylmethoxy)-
• D-SERINE, N-(ACETYLOXY)-2-METHYL-N-(PHENYLMETHYL)-, METHYL ESTER
• 4-Oxazolidinecarboxylic acid, 4-methyl-2-oxo-3-(phenylmethoxy)-, methyl ester, (4R)-
• 2-Oxazolidinone, 4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methyl-3-(phenylmethoxy)-, (4R)-

a-Methyl-D-serine Preparation Products

• a-Methyl-D-serine (81132-44-7)

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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 62-57-7(2-amino-2-methylpropanoic acid)
• 917-98-6(Alanine-1-14C,2-methyl- (6CI,7CI,8CI,9CI))
• 98019-67-1(Methanetricarboxylicacid, 1-amino-)
• 64298-94-8(2-amino-3-methoxy-2-methylpropanoic acid)
• 114396-62-2((2S)-2-Amino-3-hydroxy-2-methylpropanoic acid;hydrochloride)
• 5424-29-3(2-amino-3-hydroxy-2-methyl-propanoic acid)
• 16820-18-1(2-Methyl-L-serine)
• 26767-88-4(Propanedioic acid,2-amino-2-methyl-)
• 81133-20-2(Carbon dioxide Absorber)
• 120447-91-8(Alanine, 2-methyl-,potassium salt (1:1))