(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Basic Information

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CAS Number

23680-31-1

Molecular Formula

C15H21NO5

Molecular Weight

295.34 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

57.0 to 62.0 deg-C

Boiling Point

437.02°C (rough estimate)

Refractive Index

22 ° (C=2, EtOH)

Specific Rotation

21.5 º (c=2, ethanol)

SMILES

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CC(C)(C)OC(=O)NC(COCC1=CC=CC=C1)C(=O)O

InChI

InChI=1S/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)/t12-/m0/s1

InChIKey

DMBKPDOAQVGTST-LBPRGKRZSA-N

LogP

2.1811

Topological Polar Surface Area

84.86 Å²

Hydrogen Bond Donor/Acceptor

2 / 6

Complexity

345

Safety Information

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Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Hazard Class

Class IRRITANT Class IRRITANT

Synonyms & References

English

AM20040529
Boc-Ser(Bzl)-OH, >=99.0% (T)
AS-12200
N-tert-Butoxycarbonyl-O-benzyl-L-serine
BocSer(OBzl)
(2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid
Boc-Ser(Bzl)
(S)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid
o-Benzyl-N-(tert-butoxycarbonyl)serine #
(O-benzyl) Boc Serine
(2S)-3-Benzyloxy-2-(tert-butoxycarbonylamino)propionic acid
N-alpha-tert-BOC-o-benzyl-L-serine
J-300236
AKOS015924244
AKOS005175154
Nalpha -t-butoxycarbonyl-O-benzyl-L-serine
BOC-O-benzyl L-serine
Q-101720
Boc-Ser(OCH2C6H5)-OH
NS00050778
N-alpha-t-Butyloxycarbonyl-O-benzyl-L-serine
o-benzyl-n-(tert-butoxycarbonyl)-l-serine
D-Serine,N-(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-
N-BOC-(O-benzyl)-L-serine
MFCD00066063
BocSer(Bzl)
L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-
N-tert-butyloxycarbonyl-O-benzyl-L-serine
O-benzyl Boc-L-serine
SCHEMBL17051
AC-17187

MDL Number

MFCD00066063

FAQ

What are the physical and chemical properties of (S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid (CAS: 23680-31-1)?

(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid is a white crystalline solid with a molecular weight of approximately 340.47 g/mol. It has a low solubility in water but is more soluble in organic solvents. This compound is reactive, particularly towards nucleophiles, and can undergo esterification and amidation reactions. It is often used in peptide synthesis due to its stability and reactivity.

How is (S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid (CAS: 23680-31-1) typically synthesized?

(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid is typically synthesized via a multi-step process involving the protection of the amino group with tert-butoxycarbonyl and the introduction of the benzyloxy group. Common methods include the use of reagents like tert-butyloxycarbonyl chloride and benzylic alcohol, followed by purification techniques such as column chromatography. This compound is often synthesized with high yield and good selectivity.

What industries use (S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid (CAS: 23680-31-1)?

(S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid is primarily used in the pharmaceutical industry for peptide synthesis and drug development. It is also relevant in the polymer industry for synthesizing functional polymers and in the sensor industry for developing biosensors. Additionally, it may have applications in semiconductors, although its use in this field is less common.

What precautions should be taken when handling (S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid (CAS: 23680-31-1)?

When handling (S)-3-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid, it is important to use personal protective equipment (PPE) such as gloves, goggles, and a lab coat. This compound should be handled in a well-ventilated area, preferably under a fume hood. Spills should be cleaned up immediately using appropriate procedures, and the SDS (Safety Data Sheet) should be referenced for specific handling instructions. Storage should be in a cool, dry place away from moisture and direct sunlight.