47173-80-8

Basic information

• Product Name: N-Boc-O-Benzyl-D-serine
• Synonyms: (2R)-2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)propanoic acid;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(phenylmethoxy)propanoic acid;(2R)-2-[(tert-butoxy-oxomethyl)amino]-3-(phenylmethoxy)propanoic acid;(2R)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propionic acid;L-Serine, N-((1,1-dimethylethoxy)carbonyl)-O-(phenylmethyl)-;Boc-D-Ser(Bzl)-OH, >=98%;O-Benzyl-N-(tert-butoxycarbonyl)-D-serine;Boc-O-benzyl-D-serine≥ 99.5% (HPLC)
• CAS NO: 47173-80-8
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.33
• EINECS: 245-820-1
• Product Categories: Amino Acids;Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 47173-80-8.mol

Chemical Properties

• Melting Point: 58-60 °C(lit.)
• Boiling Point: 437.02°C (rough estimate)
• Flash Point: 229.7 °C
• Appearance: White/Powder
• Density: 1.1454 (rough estimate)
• Vapor Pressure: 4.07E-09mmHg at 25°C
• Refractive Index: -20 ° (C=2, 80% EtOH)
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Methanol
• PKA: 3.53±0.10(Predicted)
• BRN: 2665080
• CAS DataBase Reference: N-Boc-O-Benzyl-D-serine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-O-Benzyl-D-serine(47173-80-8)
• EPA Substance Registry System: N-Boc-O-Benzyl-D-serine(47173-80-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 47173-80-8(Hazardous Substances Data)

Usage

Uses

1. Chemical Synthesis and Peptide Chemistry:
N-Boc-O-Benzyl-D-serine is used as a building block in the chemical synthesis of various compounds and as a key component in peptide chemistry. Its application in this field is due to its ability to be incorporated into larger molecular structures, contributing to the development of novel pharmaceuticals and bioactive molecules.
2. Pharmaceutical Industry Cancer and Metabolic Disease Treatment:
N-Boc-O-Benzyl-D-serine is used as a precursor in the preparation of substituted naphthyl thiadiazolidinones. These compounds act as protein tyrosine phosphatase degraders, which have potential therapeutic applications in treating cancer and metabolic diseases. The degradation of these phosphatases can help regulate cellular signaling pathways, thereby providing a therapeutic approach to combat these diseases.
3. Research and Development:
In the field of research and development, N-Boc-O-Benzyl-D-serine is utilized for the synthesis of new molecules with potential biological activities. Its unique structure allows scientists to explore its properties and applications in creating innovative drugs and therapies for various medical conditions.

InChI:InChI=1/C15H21NO5/c1-15(2,3)21-14(19)16-12(13(17)18)10-20-9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,16,19)(H,17,18)/p-1/t12-/m1/s1

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 5445-44-3 O-benzylserine 
• 3850-40-6 N-Boc-DL-serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 10433-52-0 O-benzyl-D-serine 
• 3262-72-4 (R)-N-tert-butoxycarbonyl serine 
• 100-39-0 benzyl bromide 

Downstream Products

• 298713-03-8 N-Boc-O-benzyl-D,L-serine tetradecylamide 
• 139405-51-9 (S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid 2-[2-((R)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-ethoxy]-ethyl ester 

Relevant articles and documents

Subtype-Specific Agonists for NMDA Receptor Glycine Binding Sites

A series of analogues based on serine as lead structure were designed, and their agonist activities were evaluated at recombinant NMDA receptor subtypes (GluN1/2A-D) using two-electrode voltage-clamp (TEVC) electrophysiology. Pronounced variation in subunit-selectivity, potency, and agonist efficacy was observed in a manner that was dependent on the GluN2 subunit in the NMDA receptor. In particular, compounds 15a and 16a are potent GluN2C-specific superagonists at the GluN1 subunit with agonist efficacies of 398% and 308% compared to glycine. This study demonstrates that subunit-selectivity among glycine site NMDA receptor agonists can be achieved and suggests that glycine-site agonists can be developed as pharmacological tool compounds to study GluN2C-specific effects in NMDA receptor-mediated neurotransmission.

A facile synthesis of the spiroindoline-based growth hormone secretagogue, MK-677

A facile and improved route for the synthesis of the orally active spiroindoline-based growth hormone secretagogue, MK-677 was described. The key step adopted the Fischer indole/reduction strategy. The preparation of the key intermediates N-protected piperidine carboxaldehyde 5 and the N-Boc-O-benzyl-d-serine (2) are also optimized.

PYRROLOPYRROLONES ACTIVE AS KINASE INHIBITORS

Compounds represented by formula (I) wherein A, R1, R2, R3, and R4 are as defined in the specification, compositions thereof, and methods of use thereof.

GROWTH HORMONE SECRETAGOGUES

This invention relates to novel compounds which are useful in the modulation of endogenous growth hormone levels in a mammal. The invention further relates to novel intermediates for use in the synthesis of said compounds, as well as novel processes employed in these syntheses. Also included are methods of treating a mammal which include the administration of said compounds.

Synthesis and biophysical studies of modified oligonucleotides containing acyclic amino alcohol nucleoside analogs

Novel serine derivative of thymine was prepared and incorporated into oligonucleotides. These modified oligonucleotides were studied for their binding affinity with complementary DNA/RNA.

SPIRO-SUBSTITUTED AZACYCLIC DERIVATIVES AND THEIR USE AS THERAPEUTIC AGENTS

The present invention relates to compounds of formula (I), wherein n is zero, 1, 2 or 3; R represents C 1-6 alkyl, C 1-6 alkoxy, hydroxy, halogen, cyano, trifluoromethyl SO 2 C 1-6 alkyl, NR. sup.a R b, NR a COR b or CONR a R b, where R a and R b are each H, C 1-4 alkyl, phenyl or trifluoromethyl; R. sup.1 represents phenyl optionally substituted by 1, 2 or 3 of C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-4 alkyl,--O(CH 2) p O--(where p is 1 or 2) , halogen, cyano, nitro, trifluoromethyl, trimethylsilyl, OR a, SR. sup.a, SOR a, SO 2 R a, NR a R b, NR a COR b, NR a CO 2 R b, COR a, CO 2 R a or CONR a R. sup.b ; naphthyl; benzhydryl; or benyl, where the naphthyl group or each phenyl moiety of benzyl and benzhydryl may be substituted by C 1-6 alkyl, C 1-6 alkoxy, halogen or trifluoromethyl; R 2 represents hydogen, a substituent as defined for R 1 or heteroaryl selected from indazolyl, thienyl, furanyl, pyridyl, thiazolyl, tetrazolyl and quinolinyl; wherein each heteroaryl may be substituted by C 1-6 alkyl, C 1-6 alkoxy, halogen or trifluoromethyl; R 3 and R 4 are each H or C 1-6 alkyl or R 3 and R 4 together are linked so as to form a C 1-3 alkylene chain; R 5 represents H, C 1-6 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-4 alkyl, phenylC. sub.1-4 alkyl, CO 2 R a, CONR a R b, SOR a or SO 2 R a, wherein the phenyl moiety may be substituted by C. sub.1-6 alkyl, C 1-6 alkoxy, halogen or trifluoromethyl; X and Y are each H, or together represents =O; and Z represents a bond, O, S, SO, SO 2, NR 6, or--(CR 6 R 6)--where R 6 is H or C. sub.1-6 alkyl; or a pharmaceutically acceptable salt thereof. The compounds are of particular use in the treatment or prevention of pain, inflammation, migraine, emesis and postherpetic neuralgia. STR1

Amino acid nucleic acids: Synthesis and hybridization properties of a novel class of antisense oligonucleotides

Oligonucleotides containing novel phoshoramidite 12 were synthesized and studied for their hybridization properties for the first time. Interestingly, these modified oligonucleotides showed a remarkable resistance to exonuclease.

Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677

The preparation of the Merck Growth Hormone Secretagogue; MK-677 is described. A Fischer indole/reduction based strategy provides the novel spiroindoline nucleus of this potent compound. This optimized sequence necessitates the isolation of only one intermediate 10 and provides MK-677 in 48% overall yield from isonipecotic acid 3.