2152673-80-6 | 2,6-Bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$7.00	$5.00
5g	98%	in stock	$25.00	$17.00
10g	98%	in stock	$36.00	$25.00
25g	98%	in stock	$85.00	$59.00
50g	98%	in stock	$168.00	$117.00
100g	98%	in stock	$323.00	$226.00

Description

• Catalog Number: BA25656
• Chemical Name: 2,6-Bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS Number: 2152673-80-6
• Molecular Formula: C25H28BNO4
• Molecular Weight: 417.3051
• MDL Number: MFCD34182898
• SMILES: CC1(C)OB(OC1(C)C)c1ccc(nc1OCc1ccccc1)OCc1ccccc1

Upstream Synthesis Route

The synthesis of 2,6-bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine can be achieved through the following steps:

1. **Halogenation**: Begin with the 2,6-dihydroxypyridine as the starting material. Subject it to a benzylation reaction with benzyl chloride in the presence of a base such as potassium carbonate (K2CO3) to protect the hydroxyl groups. The result will be 2,6-bis(benzyloxy)pyridine.

2. **Borylation**: Next, the halogenation of 2,6-bis(benzyloxy)pyridine at the 3-position with a suitable halogenating agent such as N-bromosuccinimide (NBS) or equivalent in the presence of a Lewis acid if necessary to introduce a bromide or a chloride.

3. **Introduction of Boronate Ester**: Conduct a Suzuki coupling by treating the 3-halogenated product with bis(pinacolato)diboron in the presence of a palladium(0) catalyst and a base, typically potassium acetate (KOAc), to obtain 2,6-bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine.

4. **Purification**: Finally, purify the product using standard techniques like column chromatography.

Care should be taken to monitor reactions at each stage and ensure proper workup and isolation procedures to yield a product of high purity. Protecting group strategies and intermediate verification through NMR, IR, or mass spectrometry are critical for confirming the successful completion of each step.