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Monatin Basic information Product Name: Monatin Synonyms: Monatin;(2S,4S)-2-Amino-4-carboxy-4-hydroxy-5-(3-indolyl)pentanoic acid CAS: 146142-94-1 MF: C14H16N2O5 MW: 292.29 EINECS: -0 Product Categories: Mol File: Mol File Appearance:Sol

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Nanjing Raymon Biotech Co., Ltd.

(2s,4s)-4-amino-2-hydroxy-2-(1h-indol-3-ylmethyl)pentanedioic Acid Storage:keep in dry and cool condition Package:25kg or according to cutomer's demand Application:Chemical research/pharma intermediate Transportation:By Sea,by Air,By courier like DHL

(2s,4s)-4-amino-2-hydroxy-2-(1h-indol-3-ylmethyl)pentanedioic Acid

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Synthetic route

: (2S,4S)-4-Amino-2-(1H-indol-3-ylmethyl)-5-oxo-tetrahydro-furan-2-carboxylic acid

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol	92%
With sodium hydroxide In methanol; water at 20℃; for 6h;	54 mg
Stage #1: (2S,4S)-4-Amino-2-(1H-indol-3-ylmethyl)-5-oxo-tetrahydro-furan-2-carboxylic acid With water; potassium hydroxide In methanol at 25℃; for 1h; Inert atmosphere; Large scale reaction; Stage #2: With acetic acid In methanol pH=6.5; Large scale reaction; Stage #3: With acetic acid In methanol pH=6.5; Large scale reaction; optical yield given as %ee;	193 g

: 855433-72-6
4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)-pentanedioic acid

A: 400769-77-9
(2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid

B: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
RP18-HPLC resolution;

: 551958-84-0
4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
With pyridoxal 5'-phosphate; tris hydrochloride; monosodium glutamate; Aeromonas hydrophila IFO3820 In water; toluene at 30℃; for 16h; pH=7.6; Product distribution / selectivity; Enzymatic reaction; Culture medium;
With pyridoxal 5'-phosphate; tris hydrochloride; monosodium glutamate; Agrobacterium tumefaciens IFO3058 In water; toluene at 30℃; for 16h; pH=7.6; Product distribution / selectivity; Enzymatic reaction; Culture medium;
With pyridoxal 5'-phosphate; tris hydrochloride; monosodium glutamate; Alcaligenes faecalis ATCC8750 In water; toluene at 30℃; for 16h; pH=7.6; Product distribution / selectivity; Enzymatic reaction; Culture medium;

: 73-22-3
L-Tryptophan

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
With potassium phosphate; pyridoxal 5'-phosphate; magnesium chloride; Comamonas testosteroni proA Aldolase; HIS6-HEXaspC aminotransferase In water for 27 - 29h; pH=7.8; Product distribution / selectivity; Enzymatic reaction;
With potassium phosphate; pyridoxal 5'-phosphate; magnesium chloride; Comamonas testosteroni proA Aldolase; HIS6-HEXaspC aminotransferase In water for 27 - 29h; pH=7.8; Product distribution / selectivity; Enzymatic reaction;

: 73-22-3
L-Tryptophan

A: 914081-89-3
(S)-2-hydroxy-2-(1H-indol-3-ylmethyl)-4-oxo-pentanedioic acid

B: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
With potassium phosphate; pyridoxal 5'-phosphate; magnesium chloride; Comamonas testosteroni proA Aldolase; HIS6-HEXaspC aminotransferase In water at 30℃; for 3 - 5h; pH=7.5 - 7.8; Product distribution / selectivity; Enzymatic reaction;

: 56-41-7
L-alanin

A: 914081-89-3
(S)-2-hydroxy-2-(1H-indol-3-ylmethyl)-4-oxo-pentanedioic acid

B: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Stage #1: L-Tryptophan With potassium phosphate; pyridoxal 5'-phosphate; magnesium chloride; Comamonas testosteroni proA Aldolase; HIS6-HEXaspC aminotransferase In water at 30℃; for 3 - 5h; pH=7.5 - 7.8; Enzymatic reaction; Stage #2: L-alanin; HIS6-HEXaspC aminotransferase In water at 30℃; pH=7.5 - 7.8; Product distribution / selectivity; Enzymatic reaction;

: 113-24-6
sodium pyruvate

: 73-22-3
L-Tryptophan

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
With potassium phosphate; pyridoxal 5'-phosphate; magnesium chloride; Comamonas testosteroni proA Aldolase; HIS6-HEXaspC aminotransferase In water at 30℃; for 21 - 29h; pH=7.8; Product distribution / selectivity; Enzymatic reaction;

: 3-((2S,4S)-4-Amino-2-hydroxymethyl-5-oxo-tetrahydro-furan-2-ylmethyl)-indole-1-carboxylic acid tert-butyl ester

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C 2: 69 percent / PDC / dimethylformamide / 24 h / 20 °C 3: HCO2H; HCl / 4 h / 20 °C 4: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme

: 645396-51-6
2-[(indol-3-yl)methyl]prop-2-en-1-ol

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: CH2Cl2 / 360 h / 20 °C 2: 97 percent / imidaziole / dimethylformamide / 3 h / 20 °C 3: 97 percent / DMAP / acetonitrile / 1 h / 20 °C 4: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C 5: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure 6: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C 7: 69 percent / PDC / dimethylformamide / 24 h / 20 °C 8: HCO2H; HCl / 4 h / 20 °C 9: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1: 98 percent / MgBr2OEt2 / CH2Cl2 / 84 h / 20 °C 2: 97 percent / imidaziole / dimethylformamide / 3 h / 20 °C 3: 97 percent / DMAP / acetonitrile / 1 h / 20 °C 4: 100 percent / pyridineHF / tetrahydrofuran / 1 h / 0 °C 5: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure 6: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C 7: 69 percent / PDC / dimethylformamide / 24 h / 20 °C 8: HCO2H; HCl / 4 h / 20 °C 9: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1: CH2Cl2 / 360 h / 20 °C 2: 97 percent / imidazole / dimethylformamide 3: 97 percent / DMAP / acetonitrile 4: 100 percent / HF*pyridine / tetrahydrofuran 5: H2 / Pd(OH)2/C / methanol 6: acetonitrile 7: 69 percent / PDC / dimethylformamide 8: HCl; HCOOH 9: 92 percent / NaOH / methanol View Scheme
Multi-step reaction with 9 steps 1: 98 percent / MgBr2OEt2 / CH2Cl2 / 72 h / 20 °C 2: 97 percent / imidazole / dimethylformamide 3: 97 percent / DMAP / acetonitrile 4: 100 percent / HFpyridine / tetrahydrofuran 5: H2 / Pd(OH)2/C / methanol 6: acetonitrile 7: 69 percent / PDC / dimethylformamide 8: HCl; HCOOH 9: 92 percent / NaOH / methanol View Scheme

: 87438-91-3
ethyl 2-((1H-indol-3-yl)methyl)acrylate

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 85 percent / DIBAL-H / CH2Cl2; hexane / -78 - 20 °C 2: CH2Cl2 / 360 h / 20 °C 3: 97 percent / imidaziole / dimethylformamide / 3 h / 20 °C 4: 97 percent / DMAP / acetonitrile / 1 h / 20 °C 5: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C 6: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure 7: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C 8: 69 percent / PDC / dimethylformamide / 24 h / 20 °C 9: HCO2H; HCl / 4 h / 20 °C 10: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme
Multi-step reaction with 10 steps 1: 85 percent / DIBAL-H / CH2Cl2; hexane / -78 - 20 °C 2: 98 percent / MgBr2OEt2 / CH2Cl2 / 84 h / 20 °C 3: 97 percent / imidaziole / dimethylformamide / 3 h / 20 °C 4: 97 percent / DMAP / acetonitrile / 1 h / 20 °C 5: 100 percent / pyridineHF / tetrahydrofuran / 1 h / 0 °C 6: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure 7: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C 8: 69 percent / PDC / dimethylformamide / 24 h / 20 °C 9: HCO2H; HCl / 4 h / 20 °C 10: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme
Multi-step reaction with 11 steps 1: 97 percent / Et3N; 4-DMAP / CH2Cl2 / 20 °C 2: 72 percent / DIBAL-H / CH2Cl2 / -78 °C 3: MgBr2OEt2 / CH2Cl2 / 96 h / 20 °C 4: 97 percent / imidazole / dimethylformamide 5: 97 percent / DMAP / acetonitrile 6: 100 percent / HFpyridine / tetrahydrofuran 7: H2 / Pd(OH)2/C / methanol 8: acetonitrile 9: 69 percent / PDC / dimethylformamide 10: HCl; HCOOH 11: 92 percent / NaOH / methanol View Scheme

: 645396-53-8
(2S,5S,8aS)-2-(hydroxymethyl)-2-[(indol-3-yl)methyl]-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 97 percent / imidaziole / dimethylformamide / 3 h / 20 °C 2: 97 percent / DMAP / acetonitrile / 1 h / 20 °C 3: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C 4: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure 5: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C 6: 69 percent / PDC / dimethylformamide / 24 h / 20 °C 7: HCO2H; HCl / 4 h / 20 °C 8: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1: 97 percent / imidazole / dimethylformamide 2: 97 percent / DMAP / acetonitrile 3: 100 percent / HF*pyridine / tetrahydrofuran 4: H2 / Pd(OH)2/C / methanol 5: acetonitrile 6: 69 percent / PDC / dimethylformamide 7: HCl; HCOOH 8: 92 percent / NaOH / methanol View Scheme

Yield

Multi-step reaction with 8 steps
1: 97 percent / imidaziole / dimethylformamide / 3 h / 20 °C
2: 97 percent / DMAP / acetonitrile / 1 h / 20 °C
3: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C
4: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure
5: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C
6: 69 percent / PDC / dimethylformamide / 24 h / 20 °C
7: HCO2H; HCl / 4 h / 20 °C
8: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C
View Scheme

Multi-step reaction with 8 steps
1: 97 percent / imidazole / dimethylformamide
2: 97 percent / DMAP / acetonitrile
3: 100 percent / HF*pyridine / tetrahydrofuran
4: H2 / Pd(OH)2/C / methanol
5: acetonitrile
6: 69 percent / PDC / dimethylformamide
7: HCl; HCOOH
8: 92 percent / NaOH / methanol
View Scheme

: 645396-57-2
(2S,4S)-4-(tert-butoxycarbonyl)amino-2-[(1-(tert-butoxycarbonyl)indol-3-yl)methyl]-2-(hydroxymethyl)oxolan-5-one

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / PDC / dimethylformamide / 24 h / 20 °C 2: HCO2H; HCl / 4 h / 20 °C 3: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 69 percent / PDC / dimethylformamide 2: HCl; HCOOH 3: 92 percent / NaOH / methanol View Scheme

: 645396-58-3
(2S,4S)-4-(tert-butyloxycarbonyl)amino-2-[(1-(tert-butyloxycarbonyl)indol-3-yl)methyl]-5-oxooxolane-2-carboxylic acid

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HCO2H; HCl / 4 h / 20 °C 2: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: HCl; HCOOH 2: 92 percent / NaOH / methanol View Scheme

: 645396-59-4
(2S,5S,8aS)-2-[(tert-butyl(dimethyl)silyloxy)methyl]-2-[(indol-3-yl)methyl]-2-(hydroxymethyl)-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 97 percent / DMAP / acetonitrile / 1 h / 20 °C 2: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C 3: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure 4: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C 5: 69 percent / PDC / dimethylformamide / 24 h / 20 °C 6: HCO2H; HCl / 4 h / 20 °C 7: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1: 97 percent / DMAP / acetonitrile 2: 100 percent / HF*pyridine / tetrahydrofuran 3: H2 / Pd(OH)2/C / methanol 4: acetonitrile 5: 69 percent / PDC / dimethylformamide 6: HCl; HCOOH 7: 92 percent / NaOH / methanol View Scheme

Yield

Multi-step reaction with 7 steps
1: 97 percent / DMAP / acetonitrile / 1 h / 20 °C
2: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C
3: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure
4: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C
5: 69 percent / PDC / dimethylformamide / 24 h / 20 °C
6: HCO2H; HCl / 4 h / 20 °C
7: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C
View Scheme

Multi-step reaction with 7 steps
1: 97 percent / DMAP / acetonitrile
2: 100 percent / HF*pyridine / tetrahydrofuran
3: H2 / Pd(OH)2/C / methanol
4: acetonitrile
5: 69 percent / PDC / dimethylformamide
6: HCl; HCOOH
7: 92 percent / NaOH / methanol
View Scheme

: 645396-54-9
(2S,5S,8aS)-2-[(1-(tertbutoxycarbonyl)indol-3-yl)methyl]-2-(hydroxymethyl)-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure 2: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C 3: 69 percent / PDC / dimethylformamide / 24 h / 20 °C 4: HCO2H; HCl / 4 h / 20 °C 5: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: H2 / Pd(OH)2/C / methanol 2: acetonitrile 3: 69 percent / PDC / dimethylformamide 4: HCl; HCOOH 5: 92 percent / NaOH / methanol View Scheme

: 645396-60-7
(2S,5S,8aS)-2-[(tert-butyl(dimethyl)silyloxy)methyl]-2-[(1-(tert-butoxycarbonyl)indol-3-yl)methyl]-2-(hydroxymethyl)-5-phenyl-1,5,6,8a-tetrahydro-3,7-dioxaindolizin-8(2H)-one

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 100 percent / pyridine*HF / tetrahydrofuran / 1 h / 0 °C 2: H2 / Pd(OH)2/C / methanol / 5 h / 20 °C / atmospheric pressure 3: 15.6 mg / NaHCO3 / acetonitrile; H2O / 24 h / 20 °C 4: 69 percent / PDC / dimethylformamide / 24 h / 20 °C 5: HCO2H; HCl / 4 h / 20 °C 6: 54 mg / NaOH / methanol; H2O / 6 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: 100 percent / HF*pyridine / tetrahydrofuran 2: H2 / Pd(OH)2/C / methanol 3: acetonitrile 4: 69 percent / PDC / dimethylformamide 5: HCl; HCOOH 6: 92 percent / NaOH / methanol View Scheme

: 855436-27-0
(3S)-5-(3-indolylmethyl)-4,5-dihydroisoxazole-3,5-dicarboxylic acid

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / Na/Hg / ethanol 2: RP18-HPLC resolution View Scheme

: 855433-63-5
ethyl (3S)-5-(3-indolylmethyl)-5-carboxy-4,5-dihydroisoxazole-3-carboxylate

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: KOH / ethanol; H2O / 2.5 h / 20 °C 2: 60 percent / Na/Hg / ethanol 3: RP18-HPLC resolution View Scheme

: diethyl 5-((1H-indol-3-yl)methyl)-4,5-dihydroisoxazole-3,5-dicarboxylate

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Aspergillus oryzae protease; aq. NaOH / aq. phosphate buffer; toluene / pH 7.0 2: KOH / ethanol; H2O / 2.5 h / 20 °C 3: 60 percent / Na/Hg / ethanol 4: RP18-HPLC resolution View Scheme
Multi-step reaction with 5 steps 1.1: hydrogen; potassium hydroxide / ethanol / 1.5 h / 21 °C / 1500.15 - 3750.38 Torr / Sealed reactor; Large scale reaction 2.1: hydrogenchloride / methanol / 20 - 45 °C / Large scale reaction 2.2: 1.5 h / 5 - 25 °C / Large scale reaction 2.3: 15 h / 25 °C / Large scale reaction 3.1: protease from Bacillus lichenformis ChiroCLEC-BL / acetonitrile / 19 h / 22 °C / pH 7.5 / aq. phosphate buffer; Large scale reaction; Enzymatic reaction 4.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 1 h / 40 °C / 2250.23 Torr / Sealed vessel; Large scale reaction 5.1: water; potassium hydroxide / methanol / 1 h / 25 °C / Inert atmosphere; Large scale reaction 5.2: pH 6.5 / Large scale reaction 5.3: pH 6.5 / Large scale reaction View Scheme

Yield

Multi-step reaction with 4 steps
1: Aspergillus oryzae protease; aq. NaOH / aq. phosphate buffer; toluene / pH 7.0
2: KOH / ethanol; H2O / 2.5 h / 20 °C
3: 60 percent / Na/Hg / ethanol
4: RP18-HPLC resolution
View Scheme

Multi-step reaction with 5 steps
1.1: hydrogen; potassium hydroxide / ethanol / 1.5 h / 21 °C / 1500.15 - 3750.38 Torr / Sealed reactor; Large scale reaction
2.1: hydrogenchloride / methanol / 20 - 45 °C / Large scale reaction
2.2: 1.5 h / 5 - 25 °C / Large scale reaction
2.3: 15 h / 25 °C / Large scale reaction
3.1: protease from Bacillus lichenformis ChiroCLEC-BL / acetonitrile / 19 h / 22 °C / pH 7.5 / aq. phosphate buffer; Large scale reaction; Enzymatic reaction
4.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 1 h / 40 °C / 2250.23 Torr / Sealed vessel; Large scale reaction
5.1: water; potassium hydroxide / methanol / 1 h / 25 °C / Inert atmosphere; Large scale reaction
5.2: pH 6.5 / Large scale reaction
5.3: pH 6.5 / Large scale reaction
View Scheme

: 645396-52-7
3-(2-hydroxymethyl-allyl)-indole-1-carboxylic acid tert-butyl ester

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: MgBr2OEt2 / CH2Cl2 / 96 h / 20 °C 2: 97 percent / imidazole / dimethylformamide 3: 97 percent / DMAP / acetonitrile 4: 100 percent / HFpyridine / tetrahydrofuran 5: H2 / Pd(OH)2/C / methanol 6: acetonitrile 7: 69 percent / PDC / dimethylformamide 8: HCl; HCOOH 9: 92 percent / NaOH / methanol View Scheme
Multi-step reaction with 6 steps 1: MgBr2*OEt2 / CH2Cl2 / 96 h / 20 °C 2: H2 / Pd(OH)2/C / methanol 3: acetonitrile 4: 69 percent / PDC / dimethylformamide 5: HCl; HCOOH 6: 92 percent / NaOH / methanol View Scheme

: 645396-50-5
3-(2-ethoxycarbonyl-allyl)-indole-1-carboxylic acid tert-butyl ester

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 72 percent / DIBAL-H / CH2Cl2 / -78 °C 2: MgBr2OEt2 / CH2Cl2 / 96 h / 20 °C 3: 97 percent / imidazole / dimethylformamide 4: 97 percent / DMAP / acetonitrile 5: 100 percent / HFpyridine / tetrahydrofuran 6: H2 / Pd(OH)2/C / methanol 7: acetonitrile 8: 69 percent / PDC / dimethylformamide 9: HCl; HCOOH 10: 92 percent / NaOH / methanol View Scheme
Multi-step reaction with 7 steps 1: 72 percent / DIBAL-H / CH2Cl2 / -78 °C 2: MgBr2*OEt2 / CH2Cl2 / 96 h / 20 °C 3: H2 / Pd(OH)2/C / methanol 4: acetonitrile 5: 69 percent / PDC / dimethylformamide 6: HCl; HCOOH 7: 92 percent / NaOH / methanol View Scheme

: 3-((2S,4S)-4-Amino-2-hydroxy-2-hydroxymethyl-4-phenethyloxycarbonyl-butyl)-indole-1-carboxylic acid tert-butyl ester

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: acetonitrile 2: 69 percent / PDC / dimethylformamide 3: HCl; HCOOH 4: 92 percent / NaOH / methanol View Scheme

: 400769-77-9
(2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid

: 400769-79-1
(2S,4R)-monatin

A: 400769-81-5
(2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

B: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
With salicylaldehyde; acetic acid In methanol at 65℃; for 143h; pH=5; Product distribution / selectivity;

...Expand

: 4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutaric acid di-ammonium salt

A: 400769-81-5
(2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

B: 400769-77-9
(2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid

C: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

D: 400769-79-1
(2S,4R)-monatin

Conditions

Conditions	Yield
With ammonia; hydrogen; 5% rhodium-on-charcoal In water at 25℃; under 7500.75 Torr; for 24h; Product distribution / selectivity;

...Expand

: (2R,4S)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)-pentanedioic acid ammonium salt

: (2S,4R)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)-pentanedioic acid ammonium salt

A: 400769-81-5
(2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

B: 400769-77-9
(2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid

C: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
With methanol; salicylaldehyde; acetic acid at 80℃; for 16h; Product distribution / selectivity;

...Expand

: isoxazoline diethyl ester

A: 400769-81-5
(2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

B: 400769-77-9
(2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid

C: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

D: 400769-79-1
(2S,4R)-monatin

Conditions

Conditions	Yield
Stage #1: isoxazoline diethyl ester With potassium hydroxide; water; sponge nickel catalyst A-7063 In ethanol for 0.0833333h; Sealed reactor; Stage #2: With hydrogen In ethanol; water at 20℃; under 3750.38 Torr; for 1.5h; Product distribution / selectivity; Sealed reactor;
Stage #1: isoxazoline diethyl ester With potassium hydroxide; water In ethanol at 20℃; Stage #2: With hydrogen; sponge nickel catalyst A5200 In ethanol; water at 20℃; under 3750.38 Torr; for 2h; Product distribution / selectivity;
Stage #1: isoxazoline diethyl ester With potassium hydroxide; water In ethanol at 20℃; Stage #2: With hydrogen; 5%-palladium/activated carbon In ethanol; water at 20℃; under 3750.38 Torr; for 2h; Product distribution / selectivity;

...Expand

: isoxazoline diethyl ester

A: 400769-81-5
(2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

B: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Stage #1: isoxazoline diethyl ester With potassium hydroxide; water; sponge nickel catalyst A-7063 In ethanol at 21℃; for 0.0833333h; Sealed reactor; Stage #2: With hydrogen In ethanol under 1500.15 - 3750.38 Torr; for 1.41667h; Sealed reactor; Stage #3: With acetic acid In ethanol at 20℃; for 15h; pH=4.5; Product distribution / selectivity;

: (2S,4S) 2-benzyloxycarbonylamino-4-hydroxy-4-carboxy-5-(3-indolyl)pentanoic acid

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In methanol for 3h; Product distribution / selectivity;

: 57-60-3
piruvate

: 73-22-3
L-Tryptophan

A: 551958-84-0
4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid

B: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Stage #1: piruvate; L-Tryptophan With magnesium chloride; pyridoxal 5'-phosphate at 30℃; pH=7.5 - 7.8; Inert atmosphere; phosphate buffer; Enzymatic reaction; Stage #2: With L-alanin at 30℃; pH=7.5 - 7.8; Product distribution / selectivity; Inert atmosphere; Enzymatic reaction;

...Expand

: 535967-29-4
methyl 2-((1H-indol-3-yl)methyl)-4-(benzyloxycarbonylamino)-5-oxotetrahydrofuran-2-carboxylate

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 1 h / 40 °C / 2250.23 Torr / Sealed vessel; Large scale reaction 2.1: water; potassium hydroxide / methanol / 1 h / 25 °C / Inert atmosphere; Large scale reaction 2.2: pH 6.5 / Large scale reaction 2.3: pH 6.5 / Large scale reaction View Scheme

: 70-34-8
2,4-Dinitrofluorobenzene

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

: (2S,4S)-4-(2,4-Dinitro-phenylamino)-2-(1H-indol-3-ylmethyl)-5-oxo-tetrahydro-furan-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water Ambient temperature;

: 146142-94-1
(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

: 146029-61-0
Methyl (2S,4S)-2-(indol-3-ylmethyl)-4-(2,4-dinitroanilino)-5-oxo-2,3,4,5-tetrahydrofuran-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogen carbonate / ethanol; H2O / Ambient temperature 2: diethyl ether / 0.5 h View Scheme

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