182748-72-7 | Boc-D-Asp(OBzl)-ol

Packsize	Purity	Availability	Price	Discounted Price
250mg	95%	in stock	$36.00	$26.00
1g	95%	in stock	$96.00	$68.00
5g	95%	in stock	$473.00	$331.00
10g	95%	in stock	$775.00	$543.00
25g	95%	in stock	$1,536.00	$1,075.00

Description

• Catalog Number: AA98431
• Chemical Name: Boc-D-Asp(OBzl)-ol
• CAS Number: 182748-72-7
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.3575
• MDL Number: MFCD02094135
• SMILES: OC[C@H](NC(=O)OC(C)(C)C)CC(=O)OCc1ccccc1

Computed Properties

• Complexity: 358
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Heavy Atom Count: 22
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 9
• XLogP3: 1.6

Upstream Synthesis Route

The upstream synthesis route for Boc-D-Asp(OBzl)-ol (Boc-protected D-aspartic acid benzyl ester alcohol) involves the following steps:

1. Start with D-aspartic acid as the starting material.
2. Protect the amino group by reacting D-aspartic acid with di-tert-butyl dicarbonate (Boc₂O) in the presence of a base such as sodium hydroxide or triethylamine (TEA) to yield Boc-D-Asp-OH.
3. The carboxylic acid group of Boc-D-Asp-OH is then esterified by reaction with benzyl alcohol (BzlOH) in the presence of a coupling reagent like dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) and a catalyst such as 4-dimethylaminopyridine (DMAP). This results in the formation of Boc-D-Asp(OBzl)-OH.
4. Finally, the hydroxyl group of Boc-D-Asp(OBzl)-OH is converted to the corresponding alcohol, Boc-D-Asp(OBzl)-ol, using reducing agents like lithium aluminum hydride (LiAlH₄) or borane (BH₃) in an appropriate solvent such as tetrahydrofuran (THF).

The overall synthesis is a multi-step process that requires careful monitoring of reaction conditions, purification steps after each transformation, and characterization of intermediates to ensure the fidelity of the desired Boc-protected aspartic acid derivative.