Z(OMe)-Cys(MBzl)-OH
S-(4-methoxybenzyl)-L-cysteine
Conditions | Yield |
---|---|
With methanesulfonic acid; 3-methyl-phenol In dichloromethane at 25℃; for 0.5h; | 100% |
Multi-step reaction with 3 steps 1: aq. sodium perborate / ethyl acetate 2: CF3CO2H / diethyl ether 3: HF View Scheme |
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane 1.) 0 deg C, 1 h; 2.) RT, 30 min; | 81% |
Stage #1: p-methoxybenzyl chloride With hydrogenchloride In diethyl ether; water for 3h; Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; water at 20℃; for 2h; | 64% |
With ammonia |
Conditions | Yield |
---|---|
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In diethyl ether; water for 3h; Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2h; Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃; pH=7; | 64% |
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In diethyl ether Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2h; Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃; pH=7; | 64% |
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In diethyl ether; water for 3h; Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2h; Stage #3: With hydrogenchloride In diethyl ether; ethanol; water pH=7; | 64% |
With trifluoroacetic acid In dichloromethane |
L-Cysteine
4-methoxybenzyl hydrazinecarboxylate
S-(4-methoxybenzyl)-L-cysteine
Conditions | Yield |
---|---|
With trifluoroacetic acid |
(R)-2-(4-Methoxy-phenyl)-thiazolidine-4-carboxylic acid
S-(4-methoxybenzyl)-L-cysteine
Conditions | Yield |
---|---|
With triethylsilane; trifluoroacetic acid In dichloromethane Ambient temperature; |
(R)-2-Amino-3-(4-methoxy-phenylmethanesulfinyl)-propionic acid
S-(4-methoxybenzyl)-L-cysteine
Conditions | Yield |
---|---|
With hydrogen fluoride |
Z(OMe)-Cys(MBzl)(O)-OH
S-(4-methoxybenzyl)-L-cysteine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CF3CO2H / diethyl ether 2: HF View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; chloroform; water at 20℃; |
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.; | 100% |
With trifluoroacetic acid In dichloromethane at 20℃; Rate constant; |
di-tert-butyl dicarbonate
S-(4-methoxybenzyl)-L-cysteine
N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine
Conditions | Yield |
---|---|
Stage #1: di-tert-butyl dicarbonate; S-(4-methoxybenzyl)-L-cysteine With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h; Stage #2: With hydrogenchloride In water at 0℃; pH=3; | 99% |
Stage #1: di-tert-butyl dicarbonate; S-(4-methoxybenzyl)-L-cysteine With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h; Stage #2: With hydrogenchloride In water at 0℃; pH=3; | 99% |
With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h; | 99% |
With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h; | 99% |
In tetrahydrofuran; water Ambient temperature; pH=8; Yield given; |
Conditions | Yield |
---|---|
With Methyltrichlorosilane; 1,1'-sulfinylbisbenzene at 4℃; for 0.166667h; | 95% |
With methoxybenzene; thallium(III) trifluoroacetate In trifluoroacetic acid at 0℃; for 1h; | 86.7% |
With methoxybenzene; thallium(III) trifluoroacetate In trifluoroacetic acid at 0℃; for 1h; Product distribution; cleavage various S-protecting groups of cystein; | 86.7% |
S-(4-methoxybenzyl)-L-cysteine
(R)-2-Amino-3-(4-methoxy-phenylmethanesulfinyl)-propionic acid
L-cystine
Conditions | Yield |
---|---|
With dimethylsulfide; trifluorormethanesulfonic acid In trifluoroacetic acid at 0℃; for 1h; | 92.2% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 55℃; for 0.5h; Temperature; | 87% |
Conditions | Yield |
---|---|
With dimethylsulfide In trifluoroacetic acid at 25℃; for 1h; | 85.3% |
S-(4-methoxybenzyl)-L-cysteine
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water for 3h; | 83% |
S-(4-methoxybenzyl)-L-cysteine
N-tert-butyloxycarbonyl-L-α-aminoadipic acid α-p-methoxybenzyl ester
N-tert-butyloxycarbonyl-α-p-methoxybenzyl-δ-(L-α-aminoadipoyl)-S-p-methoxybenzyl-L-cysteine
Conditions | Yield |
---|---|
Stage #1: N-tert-butyloxycarbonyl-L-α-aminoadipic acid α-p-methoxybenzyl ester With triethylamine; isobutyl chloroformate In tetrahydrofuran at -12℃; for 0.5h; Stage #2: S-(4-methoxybenzyl)-L-cysteine With triethylamine In tetrahydrofuran; water at 0 - 20℃; for 1.83333h; | 82% |
S-(4-methoxybenzyl)-L-cysteine
2,2-dimethoxy-propane
S-<(4-methoxyphenyl)methyl>-L-cysteine methyl ester hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride | 79% |
ethanol
S-(4-methoxybenzyl)-L-cysteine
(R)-2-amino-3-(4-methoxy-benzylsulfanyl)propionic acid ethyl ester hydrochloride
Conditions | Yield |
---|---|
With acetyl chloride at 50℃; for 12h; | 69% |
S-(4-methoxybenzyl)-L-cysteine
(S)-2-(4-Methoxy-benzyloxycarbonylamino)-succinamic acid 4-nitro-phenyl ester
Z(OMe)-Asn-Cys(MBzl)-OH
Conditions | Yield |
---|---|
With triethylamine In water; N,N-dimethyl-formamide for 24h; Ambient temperature; | 57% |
S-(4-methoxybenzyl)-L-cysteine
Conditions | Yield |
---|---|
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃; | 41% |
Conditions | Yield |
---|---|
With dimethylsulfide; trifluorormethanesulfonic acid In trifluoroacetic acid at 0℃; for 1h; | 15.5% |
N-(tert-butyloxycarbonyl) azide
S-(4-methoxybenzyl)-L-cysteine
N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine
S-(4-methoxybenzyl)-L-cysteine
N-(4-methoxybenzyloxycarbonyl)-α-(4-methoxybenzylester)-δ-L-α-aminoadipic acid
<(N-4-methoxybenzyloxycarbonyl)-(α-4-methoxybenzyl)-δ-(L-α-aminoadipoyl)>-S-(4-methoxybenzyl)-L-cysteine
Conditions | Yield |
---|---|
With triethylamine; isobutyl chloroformate 1) THF, -15 deg C, 30 min, 2) H2O, RT, 50 min; Yield given. Multistep reaction; | |
With triethylamine; isobutyl chloroformate 1) THF; Multistep reaction; |
S-(4-methoxybenzyl)-L-cysteine
Boc-Lys(Z)-Thr-Phe-Thr-Ser-NHNH2
Boc-Lys(Z)-Thr-Phe-Thr-Ser-Cys(MBzl)-OH
Conditions | Yield |
---|---|
With hydrogenchloride; tert.-butylnitrite; triethylamine 1) THF, DMF, 15 min, -15 deg C 2) THF, DMF, 0 deg C, 24 h, room temp.,48 h; Yield given. Multistep reaction; |
S-(4-methoxybenzyl)-L-cysteine
2,2-dimethoxy-propane
S-p-methoxybenzyl-L-cysteine methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; sodium carbonate Multistep reaction; |
S-(4-methoxybenzyl)-L-cysteine
Z(OMe)-Ser-NHNH2
Z(OMe)-Ser-Cys(CH2PhOMe)-OH
Conditions | Yield |
---|---|
(i) isopentyl nitrite, HCl, (ii) /BRN= 2055074/, aq. Et3N; Multistep reaction; |
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane |
S-(4-methoxybenzyl)-L-cysteine
H-Asn-Cys(MBzl)-OH
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 57 percent / Et3N / dimethylformamide; H2O / 24 h / Ambient temperature 2: TFA-anisole View Scheme |
S-(4-methoxybenzyl)-L-cysteine
H-Cys(MBzl)-Asn-Cys(MBzl)-OMe
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 57 percent / Et3N / dimethylformamide; H2O / 24 h / Ambient temperature 2: TFA-anisole 3: 82 percent / Et3N / dimethylformamide / 12 h / Ambient temperature 4: 88 percent / dimethylformamide; diethyl ether 5: TFA-anisole View Scheme |
The L-Cysteine,S-[(4-methoxyphenyl)methyl]-, with the CAS registry number 2544-31-2, is also known as S-(4-Methoxybenzyl)-L-cysteine and H-Cys(pMeOBzl)-OH. It belongs to the product categories of Pharmaceutical Intermediates; Amino Acids Derivatives; Amino Acids; Cysteine [Cys, C]; Amino Acids and Derivatives. This chemical's molecular formula is C11H15NO3S and molecular weight is 241.31. What's more, its systematic name is called (2R)-2-Ammonio-3-[(4-methoxybenzyl)sulfanyl]propanoate.
Physical properties about L-Cysteine,S-[(4-methoxyphenyl)methyl]- are: (1) ACD/LogP: 2.01; (2) # of Rule of 5 Violations: 0; (3) ACD/LogD (pH 5.5): -0.49; (4) ACD/LogD (pH 7.4): -0.52; (5) ACD/BCF (pH 5.5): 1; (6) ACD/BCF (pH 7.4): 1; (7) ACD/KOC (pH 5.5): 1; (8) ACD/KOC (pH 7.4): 1; (9) #H bond acceptors: 4; (10) #H bond donors: 3; (11) #Freely Rotating Bonds: 7; (12) Polar Surface Area: 71.83 Å2; (13) Index of Refraction: 1.59; (14) Molar Refractivity: 64.8 cm3; (15) Molar Volume: 191.9 cm3; (16) Surface Tension: 53.4 dyne/cm; (17) Density: 1.257 g/cm3; (18) Flash Point: 206.4 °C; (19) Enthalpy of Vaporization: 70.74 kJ/mol; (20) Boiling Point: 417.6 °C at 760 mmHg; (21) Vapour Pressure: 1.01E-07 mmHg at 25 °C.
Preparation of L-Cysteine,S-[(4-methoxyphenyl)methyl]-: this chemical can be prepared by 1-Chloromethyl-4-methoxy-benzene with L-cysteine.
This reaction needs reagent TFA and solvent CH2Cl2 at temperature of 0 °C. The reaction time is 30 min. The yield is 81 %.
Uses of L-Cysteine,S-[(4-methoxyphenyl)methyl]-: it can react with S-(4-Methoxybenzyl)-L-cysteine to give L-Cysteine.
The reaction occurs with reagent CF3CO2H and solvent CH2Cl2 at temperature of 20 °C.
You can still convert the following datas into molecular structure:
(1) SMILES:[O-]C(=O)[C@@H]([NH3+])CSCc1ccc(OC)cc1
(2) InChI: InChI=1/C11H15NO3S/c1-15-9-4-2-8(3-5-9)6-16-7-10(12)11(13)14/h2-5,10H,6-7,12H2,1H3,(H,13,14)/t10-/m0/s1
(3) InChIKey:PQPZSPJVMUCVAQ-JTQLQIEIBO
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