58290-35-0

Basic information

• Product Name: Boc-S-4-methoxybenzyl-D-cysteine
• Synonyms: N-alpha-t-Butyloxycarbonyl-S-(4-methoxy-benzyl)-D-cysteine;(R)-2-(Tert-butoxycarbonylamino)-3-(4-methoxybenzylthio)propanoic acid;Boc-Cys(pMeOBzl)-OH;Boc-S-(4-methoxybenzyl)-D-cysteine;Boc-D-Cys(4-Mob)-OH Boc-S-4-Methoxybenzyl-D-cysteine;N-Boc-S-(4-Methoxybenzyl)-D-cysteine, 95%;Boc-S-4-methoxybenzyl-D-cysteine≥ 98% (HPLC);(Tert-Butoxy)Carbonyl D-Cys(pMeOBzl)-OH
• CAS NO: 58290-35-0
• Molecular Formula: C16H23NO5S
• Molecular Weight: 341.42
• Mol File: 58290-35-0.mol

Chemical Properties

• Boiling Point: 514 °C at 760 mmHg
• Flash Point: 264.7 °C
• Appearance: /
• Density: 1.205 g/cm³
• Storage Temp.: Store at RT.
• CAS DataBase Reference: Boc-S-4-methoxybenzyl-D-cysteine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-S-4-methoxybenzyl-D-cysteine(58290-35-0)
• EPA Substance Registry System: Boc-S-4-methoxybenzyl-D-cysteine(58290-35-0)

Safety Data

• Hazardous Substances Data: 58290-35-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2544-31-2 S-(4-methoxybenzyl)-L-cysteine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 222404-25-3 (R)-2-(4-Methoxy-phenyl)-thiazolidine-4-carboxylic acid 
• 76614-97-6 ammonium chloride salt of S-p-methoxybenzyl-(2R)-cysteine 
• 10389-65-8 di-t-butoxycarbonyl-L-cystine 
• 824-94-2 p-methoxybenzyl chloride 
• 20887-95-0 N-(tert-Butyloxycarbonyl)-L-cysteine 

Downstream Products

• 97507-31-8 Boc-Cys(MBzl)-Gly-OBzl 
• 86895-15-0 Boc-Cys(MBzl)-Ala-Gly-OMe 
• 97507-32-9 Boc-Cys(MBzl)-γ-Glu(OBzl)-Cys(MBzl)-Gly-OBzl 
• 97507-18-1 Boc-L-Cys(MBzl)-L-Glu-OBzl(Gly-OBzl) 
• 97507-21-6 Boc-L-Cys(MBzl)-D-Cys(MBzl)-L-Glu-OBzl(Gly-OBzl) 
• 58171-85-0 Boc-Cys(PMB)-OTcp 
• 97588-91-5 Boc-D-Cys(MBzl)-L-Glu-OBzl(Gly-OBzl) 
• 97507-19-2 Boc-D-Cys(MBzl)-L-Cys(MBzl)-L-Glu-OBzl(Gly-OBzl) 
• 108562-90-9 Boc-Cys(MBzl)-NHMe 
• 183741-33-5 [(R)-2-[4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidin-1-yl]-1-(4-methoxy-benzylsulfanylmethyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

A comprehensive one-pot synthesis of protected cysteine and selenocysteine SPPS derivatives

A proof-of-principle methodology is presented in which all commercially-available cysteine (Cys) and selenocysteine (Sec) solid phase peptide synthesis (SPPS) derivatives are synthesized in high yield from easily prepared protected dichalcogenide precursors. A Zn-mediated biphasic reduction process applied to a series of four bis-Nα-protected dichalcogenide compounds allows facile conversion to their corresponding thiol and selenol intermediates followed by insitu S- or Se-alkylation with various electrophiles to directly access twenty one known Cys and Sec SPPS derivatives. Most of these derivatives were able to be precipitated in crude form out of petroleum ether in sufficient purity for direct use as peptide building blocks. Subsequent incorporation of these derivatives into peptide models nicely illustrates their viability and applicability toward SPPS.

Synthesis, characterization and antioxidant activity of angiotensin converting enzyme inhibitors

Angiotensin converting enzyme (ACE) catalyzes the conversion of angiotensin I (Ang I) to angiotensin II (Ang II). ACE also cleaves the terminal dipeptide of vasodilating hormone bradykinin (a nonapeptide) to inactivate this hormone. Therefore, inhibition of ACE is generally used as one of the methods for the treatment of hypertension. 'Oxidative stress' is another disease state caused by an imbalance in the production of oxidants and antioxidants. A number of studies suggest that hypertension and oxidative stress are interdependent. Therefore, ACE inhibitors having antioxidant property are considered beneficial for the treatment of hypertension. As selenium compounds are known to exhibit better antioxidant behavior than their sulfur analogues, we have synthesized a number of selenium analogues of captopril, an ACE inhibitor used as an antihypertensive drug. The selenium analogues of captopril not only inhibit ACE activity but also effectively scavenge peroxynitrite, a strong oxidant found in vivo. The Royal Society of Chemistry 2011.

INDOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS

The present invention relates to new indole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole compounds as an active ingredient.

GLUCOKINASE ACTIVATORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to new compounds of formula (1) exhibiting excellent activity for glucokinase, and pharmaceutical compositions comprising the same as an active ingredient.

INDOLE AND INDAZOLE DERIVATIVES HAVING A CELL-, TISSUE- AND ORGAN-PRESERVING EFFECT

The present invention relates to a composition for preserving cells, tissues and organs, comprising as an active ingredient indole and indazole compounds of formula (1), or a pharmaceutically acceptable salt or isomer thereof, which are effective for preventing injury of organs, isolated cell systems or tissues caused by cold storage, transplant operation or post-transplantation reperfusion; a preservation method; and a preparation method of the composition.

GLUCOKINASE ACTIVATORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to new compounds of formula (1) exhibiting excellent activity for glucokinase, and pharmaceutical compositions comprising the same as an active ingredient.

INDOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS

The present invention relates to new indole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole compounds as an active ingredient.

Selective detachment of Boc-protected amino acids and peptides from Merrifield, PAM and Wang resins by trimethyltin hydroxide

We describe the development of a new non-acidolytic and non- nucleophilic method for the selective cleavage by trimethyltin hydroxide of amino acids and dipeptides at benzyl ester links attached to resins commonly used in peptide synthesis.

Two new procedures for the introduction of benzyl-type protecting groups for thiols

Two new methods for the benzylation of thiols are described: a) direct-S- alkylation with para-substituted benzylic cations; and b) reductive S- alkylations of 2-aminothiols. Both methods provide efficient routes for the introduction of benzyl-type protecting groups in high yields.

Oxidative Deblocking of the 4-Methoxybenzyl Thioether Protecting Group: Application to the Directed Synthesis of Poly-cystinyl Peptides

The 4-methoxybenzyl thioether protecting group is deblocked efficiently by oxidation with the homogeneous electron transfer agent tris(4-bromophenyl)ammoniumyl (2.+) leading to the disulfide in high yields.S-(4-methoxybenzyl)cysteine derivatives like 9 in this way can be transformed into the corresponding cystine derivatives like 10 in 90percent yield.Many N and carboxy protecting groups like the Boc and Z group and tert-butyl or benzyl ester functions are stable under the cleavage conditions.On the other hand the 4-methoxybenzyl thioether protecting group is totally unaffected by the conditions for oxidative deblocking of the S-trityl functions by either iodine or rhodanolysis.This opens up new opportunities for the directed synthesis of cystinyl peptides with more than one intra- or interchain disulfide bridge.Application of the new method to the synthesis of a cystine peptide with one intrachain S-S-bridge and a double-chain biscystinyl peptide is reported.