3,5-bis((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-N-(prop-2-ynyl)benzamide

Base Information

• Chemical Name: 3,5-bis((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-N-(prop-2-ynyl)benzamide
• CAS No.: 916084-85-0
• Molecular Formula: C₂₄H₄₁NO₄Si₂
• Molecular Weight: 463.765
• Mol file: 916084-85-0.mol

Synonyms:3,5-bis((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-N-(prop-2-ynyl)benzamide

Chemical Property of 3,5-bis((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-N-(prop-2-ynyl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-bis((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-N-(prop-2-ynyl)benzamide

There total 3 articles about 3,5-bis((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-N-(prop-2-ynyl)benzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

4-hydroxy-3,5-bis(hydroxymethyl)-N-(prop-2-ynyl)benzamide (916084-84-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 3,5-bis((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-N-(prop-2-ynyl)benzamide (916084-85-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1002/chem.200601263 DOI:10.1016/j.bmc.2007.08.046

Reference yield:

4-hydroxy-benzoic acid (99-96-7) → 3,5-bis((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-N-(prop-2-ynyl)benzamide (916084-85-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide; 1-hydroxybenzotriazole / dimethylformamide

2: 80 percent / NaOH / H₂O / 72 h / 55 °C

3: 80 percent / imidazole / dimethylformamide / 2 h / 20 °C

With 1H-imidazole; sodium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In water; N,N-dimethyl-formamide;

DOI:10.1002/chem.200601263

Reference yield:

4-hydroxy-N-(prop-2-ynyl)benzamide (750624-40-9) → 3,5-bis((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-N-(prop-2-ynyl)benzamide (916084-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NaOH / H₂O / 72 h / 55 °C

2: 80 percent / imidazole / dimethylformamide / 2 h / 20 °C

With 1H-imidazole; sodium hydroxide; In water; N,N-dimethyl-formamide;

DOI:10.1002/chem.200601263

upstream raw materials:

4-hydroxy-3,5-bis(hydroxymethyl)-N-(prop-2-ynyl)benzamide

tert-butyldimethylsilyl chloride

4-hydroxy-benzoic acid

4-hydroxy-N-(prop-2-ynyl)benzamide

Downstream raw materials:

methyl-(2-{methyl-[4-prop-2-ynylcarbamoyl-2,6-bis-(quinolin-6-ylcarbamoyloxymethyl)-phenoxycarbonyl]-amino}-ethyl)-carbamic acid 4-[bis-(2-tert-butoxycarbonylamino-ethyl)-carbamoyloxy]-benzyl ester

C₃₆H₃₇N₅O₁₅

(2-{[2,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-prop-2-ynylcarbamoyl-phenoxycarbonyl]-methyl-amino}-ethyl)-methyl-carbamic acid tert-butyl ester

{2-[(2,6-bis-hydroxymethyl-4-prop-2-ynylcarbamoyl-phenoxycarbonyl)-methyl-amino]-ethyl}-methyl-carbamic acid tert-butyl ester