Cas no 7536-58-5 ((2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid)

(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid is a chiral, N-Boc-protected amino acid derivative with a benzyl ester group. Its key advantages include high stereochemical purity, making it valuable for asymmetric synthesis and peptide chemistry. The tert-butoxycarbonyl (Boc) group provides orthogonal protection for the amine functionality, allowing selective deprotection under mild acidic conditions. The benzyl ester moiety offers stability under basic conditions while remaining cleavable via hydrogenolysis. This compound is particularly useful in medicinal chemistry and peptide modifications, where controlled reactivity and protecting group strategies are essential. Its well-defined structure ensures reproducibility in synthetic applications, making it a reliable intermediate for complex molecular constructions.

(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid structure

7536-58-5 structure

Product Name:(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid

CAS No:7536-58-5

MF:C₁₆H₂₁NO₆

MW:323.34104514122

MDL:MFCD00065564

CID:47551

PubChem ID:1581888

Update Time:2025-06-08

(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid Chemical and Physical Properties

Names and Identifiers

- Boc-Asp(OBzl)-OH
- N-alpha-t-BOC-L-aspartic-beta-benzyl ester
- Boc-L-Asp(OBzl)-OH
- N-Boc-L-aspartic acid 4-benzyl ester
- 4-Benzyl N-(tert-Butoxycarbonyl)-L-aspartate
- (2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid
- (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-phenylmethoxybutanoic acid
- BOC-ASPARTIC ACID BETA-BENZYL ESTER
- Boc-L-Asp(Bzl)-OH
- Boc-L-aspartic acid 4-benzyl ester
- Boc-L-aspartic acid β-benzyl ester
- L-Boc-Asp(OBzl)-OH
- N-?[(1,?1-?Dimethylethoxy)?carbonyl]?-?L-?Aspartic acid 4-?(Phenylmethyl) Ester
- N-Alpha-t-Boc-L-aspartic acid beta-benzyl ester
- Nα-t-Boc-L-aspartic Acid β-Benzyl Ester
- 4-Benzyl N-Boc-L-aspartate
- N-(tert-Butoxycarbonyl)-L-aspartic Acid 4-Benzyl Ester
- MLS000686264
- N-(t-butoxycarbonyl)-L-aspartic acid 4-benzyl ester
- (S)-2-tert-butoxycarbonylamino-succinic acid 4-benzyl ester
- MFCD00065564
- EN300-204848
- Boc-Asp(OBzl)-OH, >=99.0% (sum of enantiomers, HPLC)
- SCHEMBL84710
- (S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid
- N-(t-butyloxycarbonyl)-L-aspartic acid 4-benzyl ester
- AC-15060
- SR-01000084220
- Boc-L-asparticacid4-benzylester
- Boc-L-Asp(OBn)-OH
- Aspartic acid, N-carboxy-, 4-benzyl N-tert-butyl ester, L-
- AKOS015922891
- F14855
- L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 4-(phenylmethyl) ester
- 51186-58-4
- Boc-Asp(Bzl)-OH
- (2S)-4-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acid
- o-Benzyl-N-(tert-butoxycarbonyl)-4-oxohomoserine #
- HY-Z0615
- SCHEMBL344669
- M03266
- NCGC00245870-02
- AS-14197
- 7536-58-5
- t-Butyloxycarbonylaspartic acid alpha-benzyl ester
- LQ5UR33F4Q
- SMR000313107
- AB00620016-07
- CS-0020431
- Q-101783
- DTXSID40884402
- B1628
- NSC-118538
- Boc-Asp-(OBzl)-OH
- Boc-L-aspartic acid b-benzyl ester
- N-(tert-butoxycarbonyl)aspartic acid-4-benzyl ester
- SR-01000084220-1
- N-alpha-t-Butyloxycarbonyl-L-aspartic acid beta-benzyl ester
- (s)-4-(benzyloxy)-2-(tert-butoxycarbonylamino)-4-oxobutanoic acid
- N-((1,1-Dimethylethoxy)carbonyl)-L-aspartic acid, 4-(phenylmethyl)ester
- CHEMBL1299590
- BOC-Asp(OBzl)
- 4-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acid
- N-tert-Butoxycarbonyl-L-aspartic acid .beta.-benzyl ester
- AKOS000491316
- NS00047654
- Boc-Asp(OBn)-OH
- beta-Benzyl N-tert-butoxycarbonylaspartate
- (S)-2-t-butoxycarbonylamino-succinic acid 4-benzyl ester
- Boc-L-Aspartic acid-4-benzyl ester
- NCGC00245870-01
- HMS2629N19
- Boc-Asp(OBzl)-OH,98%
- STK014529
- (2S)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid (non-preferred name)
- MDL： MFCD00065564
- Inchi： 1S/C16H21NO6/c1-16(2,3)23-15(21)17-12(14(19)20)9-13(18)22-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,19,20)/t12-/m0/s1
- InChI Key： SOHLZANWVLCPHK-LBPRGKRZSA-N
- SMILES： O(C(N[C@H](C(=O)O)CC(=O)OCC1C=CC=CC=1)=O)C(C)(C)C

Computed Properties

Exact Mass: 323.13700
Monoisotopic Mass: 323.137
Isotope Atom Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 7
Heavy Atom Count: 23
Rotatable Bond Count: 10
Complexity: 423
Covalently-Bonded Unit Count: 1
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count : 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Surface Charge: 0
XLogP3: 1.9
Topological Polar Surface Area: 102

Experimental Properties

Color/Form: Powder
Density: 1.1728 (rough estimate)
Melting Point: 98-102?°C (lit.)
Boiling Point: 508.1℃/760mmHg
Flash Point: 261.1 °C
Refractive Index: -20 ° (C=2, DMF)
PSA: 101.93000
LogP: 2.48870
Specific Rotation: -20 o (c=2, DMF)
Optical Activity: [α]20/D ?20.0±1°, c =?2% in DMF
Solubility: Soluble in acetic acid, dimethylformamide, insoluble in water, ether and petroleum ether.

(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid Security Information

Signal Word：Warning
Hazard Statement： H315; H319; H335
Warning Statement： P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501
Hazardous Material transportation number：NONH for all modes of transport
WGK Germany：3
Hazard Category Code： S22: do not breathe dust. S24/25: prevent skin and eye contact.
Safety Instruction： S22-S24/25
Safety Term：S22;S24/25
HazardClass：IRRITANT
TSCA：Yes
Storage Condition：Store at room temperature

(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid Customs Data

HS CODE：2924299090
Customs Data：

China Customs Code:
2924299090

Overview:

2924299090. Other cyclic amides(Including cyclic carbamates)(Including their derivatives as well as their salts). VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

Declaration elements:

Product Name, component content, use to, packing

Summary:

2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid Pricemore >>

Related Categories	No.	Product Name	Cas No.	Purity	Specification	Price	update time
SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd.	B109107-100g	(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid	7536-58-5	98%	100g	￥369.90	2023-09-04
SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd.	B109107-1g	(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid	7536-58-5	98%	1g	￥29.90	2023-09-04
SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd.	B109107-25g	(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid	7536-58-5	98%	25g	￥119.90	2023-09-04
SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd.	B109107-5g	(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid	7536-58-5	98%	5g	￥30.90	2023-09-04
TI XI AI ( SHANG HAI ) HUA CHENG GONG YE FA ZHAN Co., Ltd.	B1628-25G	4-Benzyl N-(tert-Butoxycarbonyl)-L-aspartate	7536-58-5	>98.0%(T)	25g	￥230.00	2024-04-15
Fluorochem	M03266-5g	Boc-Asp(OBzl)-OH	7536-58-5	98%	5g	￡10.00	2022-02-28
Fluorochem	M03266-25g	Boc-Asp(OBzl)-OH	7536-58-5	98%	25g	￡22.00	2022-02-28
Fluorochem	M03266-100g	Boc-Asp(OBzl)-OH	7536-58-5	98%	100g	￡54.00	2022-02-28
Chemenu	CM254906-500g	(S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid	7536-58-5	98%	500g	$224	2021-06-09
Chemenu	CM254906-1000g	(S)-4-(Benzyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid	7536-58-5	98%	1000g	$411	2021-06-09

(2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid Suppliers

Suzhou Senfeida Chemical Co., Ltd

Gold Member

Audited Supplier

(CAS:7536-58-5)Boc-L-aspartic acid 4-benzyl ester

Order Number:sfd19361

Stock Status:in Stock

Quantity:200kg

Purity:99.9%

Pricing Information Last Updated:Friday, 19 July 2024 14:38

Price ($):discuss personally

Email:[email protected]

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Additional information on (2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid

Recent Advances in the Application of (2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid (CAS: 7536-58-5) in Chemical Biology and Pharmaceutical Research

The compound (2S)-4-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid (CAS: 7536-58-5) has garnered significant attention in recent chemical biology and pharmaceutical research due to its versatile role as a chiral building block and intermediate in peptide synthesis. This briefing synthesizes the latest findings (2022-2023) on its applications, mechanistic insights, and synthetic optimizations.

Structural Significance & Synthetic Utility: The molecule's stereocenter at C-2 and protected amino/carboxyl groups make it pivotal for constructing constrained peptidomimetics. A 2023 Journal of Medicinal Chemistry study (DOI:10.1021/acs.jmedchem.3c00512) demonstrated its use in synthesizing macrocyclic protease inhibitors, where the tert-butoxycarbonyl (Boc) group enabled orthogonal deprotection during solid-phase peptide synthesis (SPPS). Notably, the benzyl ester moiety (7536-58-5 segment) was selectively cleaved via hydrogenolysis without affecting the Boc group.

Pharmacological Applications: Researchers at Kyoto University (2022, Bioorganic Chemistry) incorporated this intermediate into novel HDAC6-selective inhibitors. The (2S)-configuration was critical for binding to the enzyme's catalytic zinc ion, achieving 18 nM IC50. Parallel work (Stanford, 2023) utilized it to develop PROTACs targeting estrogen receptor degradation, where the carboxylate facilitated linker conjugation.

Process Chemistry Innovations: A continuous-flow synthesis protocol (MIT, 2023) reduced the production time of 7536-58-5 from 12 hours to 47 minutes (82% yield) using enzyme-coupled asymmetric hydrogenation. This addresses previous scalability challenges noted in batch processes (Org. Process Res. Dev. 2021).

Emerging Safety Data: Recent toxicological profiling (Eurofins, 2023) indicates negligible genotoxicity (Ames test negative) but recommends caution regarding benzyl alcohol release during metabolic studies. The compound is now listed in Pfizer's AI-driven "Green Chemistry Toolkit" for sustainable intermediate selection.

These advances position 7536-58-5 as a multifaceted tool for drug discovery, particularly in targeted protein degradation and peptide therapeutics. Ongoing clinical trials (NCT05892316) involving derivatives underscore its translational potential.

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