188476-33-7

Basic information

• Product Name: N-BOC-ALPHA-METHYL-D-SERINE METHYL ESTER
• Synonyms: N-BOC-ALPHA-METHYL-D-SERINE METHYL ESTER;N-BOC-A-METHYL -D-SERINE METHYL ESTER;N-Boc-2-Methyl-D-serine Methyl ester, 97%;(S)-2-(tert-ButoxycarbonylaMino)-3-hydroxy-2-Methylpropanoic acid Methyl ester
• CAS NO: 188476-33-7
• Molecular Formula: C₁₀H₁₉NO₅
• Molecular Weight: 233.26
• Mol File: 188476-33-7.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-BOC-ALPHA-METHYL-D-SERINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-ALPHA-METHYL-D-SERINE METHYL ESTER(188476-33-7)
• EPA Substance Registry System: N-BOC-ALPHA-METHYL-D-SERINE METHYL ESTER(188476-33-7)

Safety Data

• Hazardous Substances Data: 188476-33-7(Hazardous Substances Data)

Usage

General Description

N-BOC-ALPHA-METHYL-D-SERINE METHYL ESTER is a chemical compound that is commonly used in the synthesis of peptides and pharmaceuticals. It is a derivative of the amino acid D-serine and is frequently employed as a building block in organic and medicinal chemistry. N-BOC-ALPHA-METHYL-D-SERINE METHYL ESTER is often utilized as a protecting group for the amino group in peptide synthesis, allowing for selective deprotection and functionalization. It is important for the development of new drug compounds and has potential applications in the pharmaceutical industry.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 177270-59-6 (S)-2-tert-Butoxycarbonylamino-3-methoxymethoxy-2-methyl-propionic acid methyl ester 
• 147316-32-3 (2S)-methyl 2-amino-3-hydroxy-2-methylpropanoate 
• 186581-53-3 diazomethane 
• 84311-19-3 (S)-2-tert-Butoxycarbonylamino-3-hydroxy-2-methyl-propionic acid 
• 3398-40-1 (S)-(+)-2-amino-2-methyl-3-hydroxypropanoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 74-88-4 methyl iodide 
• 902451-76-7 3-tert-butyl 4-methyl (S)-4-methyl-2-oxooxazolidine-3,4-dicarboxylate 
• 902451-75-6 methyl (S)-4-methyl-2-oxooxazolidine-4-carboxylate 
• 902451-73-4 methyl (R)-3-carbamoyloxy-2-methylpropanoate 
• 942150-87-0 C₁₃H₁₇NO₇S 
• 72657-23-9 methyl (R)-3-hydroxy-2-methylpropionate 
• 909023-95-6 ((1S,2S)-2,3-Dihydroxy-1-hydroxymethyl-1-methyl-propyl)-carbamic acid tert-butyl ester 

Downstream Products

• 205817-26-1 (S)-3-Benzyloxyamino-2-tert-butoxycarbonylamino-2-methyl-propionic acid methyl ester 

Relevant articles and documents

Facile stereospecific synthesis and biological evaluation of (S)- and (R)-2-amino-2-methyl-4-[123I]iodo-3-(E)-butenoic acid for brain tumor imaging with single photon emission computerized tomography

Both enantiomers of 2-amino-2-methyl-4-iodo-3-(E)-butenoic acid (IVAIB, 5) were radioiodoinated in 65-72% yield. (S)-IVAIB entered 9L gliosarcoma cells primarily via A-type transport in vitro with higher uptake than (R)-IVAIB. Biodistribution studies in rats with 9L gliosarcoma brain tumors demonstrated higher tumor to brain ratios with (S)-IVAIB (75:1 at 1 h) than (R)-IVAIB (7.7:1). In this model, (S)-IVAIB is superior to (R)-IVAIB and is a promising radiotracer for brain tumor imaging.

Complementary syntheses of N,O-protected-(S)-2-methylserine on a multikilogram scale

Two complementary and scalable approaches have been used to manufacture multikilogram quantities of N,O-protected-(S)-2-methylserine. The first approach uses a diastereomeric salt resolution of 2-methylserine methyl ester as the (1S)-(+)-camphorsulfonate salt, and was used to rapidly access 15 kg of (S)-3-tert-butoxycarbonyl-2,2,4-trimethyl-1,3-oxazolidine-4-carboxylic acid with >99% ee. The second approach involves a stereoselective enolate methylation of a chiral cyclic l-serine derivative under cryogenic conditions. The four-step telescoped process, starting from l-serine methyl ester, was used to manufacture 20 kg of (2R,4S)-2-tert-butyl-3-tert-butoxycarbonyl-4-methyl-1,3- oxazolidine-4-carboxylic acid in 52% overall yield and 98% ee. The advantages and disadvantages for scale-up of both approaches are discussed.

AGONISTS OF THE SPHINGOSINE- 1- PHOSPHATE RECEPTOR (SLP)

The invention provides compounds of formula I and formula II, their preparation, a their use as pharmaceutically active immunosuppressive agents for the treatment of autoimmune disorders, organ transplant rejection, disorders associated with an activated immune system, as well as other disorders modulated by lymphopenia or SlP receptors.