2-(2-tert-butyl-dimethylsilyl-oxyethyl)-2-tetrahydrofuroic acid, benzyl ester

Base Information

• Chemical Name: 2-(2-tert-butyl-dimethylsilyl-oxyethyl)-2-tetrahydrofuroic acid, benzyl ester
• CAS No.: 327618-58-6
• Molecular Formula: C₂₀H₃₂O₄Si
• Molecular Weight: 364.557
• Mol file: 327618-58-6.mol

Synonyms:

Chemical Property of 2-(2-tert-butyl-dimethylsilyl-oxyethyl)-2-tetrahydrofuroic acid, benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-tert-butyl-dimethylsilyl-oxyethyl)-2-tetrahydrofuroic acid, benzyl ester

There total 1 articles about 2-(2-tert-butyl-dimethylsilyl-oxyethyl)-2-tetrahydrofuroic acid, benzyl ester 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:

2-tert-butyldimethylsilyloxyethyl iodide (101166-65-8) + benzyl (+/-)-tetrahydrofuran-2-carboxylate (78277-21-1) → 2-(2-tert-butyl-dimethylsilyl-oxyethyl)-2-tetrahydrofuroic acid, benzyl ester (327618-58-6)

Guidance literature:

With lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0960-894X(02)00211-1

Reference yield:

2-(2-tert-butyl-dimethylsilyl-oxyethyl)-2-tetrahydrofuroic acid, benzyl ester (327618-58-6) → 3-(2',6'-dimethoxy-biphenyl-4-yl)-2-{[2-(2-oxo-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: H₂; Et₃N / Pd/C / methanol

2: PyBOP; DIPEA / CH₂Cl₂

3: TBAF / tetrahydrofuran

4: oxalyl chloride; DMSO

With oxalyl dichloride; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 4: Swern oxidation;

DOI:10.1016/S0960-894X(02)00211-1

Reference yield:

2-(2-tert-butyl-dimethylsilyl-oxyethyl)-2-tetrahydrofuroic acid, benzyl ester (327618-58-6) → 3-(2',6'-dimethoxy-biphenyl-4-yl)-2-{[2-(2-methoxy-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid tert-butyl ester (327618-63-3)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂; Et₃N / Pd/C / methanol

2: PyBOP; DIPEA / CH₂Cl₂

3: TBAF / tetrahydrofuran

With tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0960-894X(02)00211-1

upstream raw materials:

2-tert-butyldimethylsilyloxyethyl iodide

benzyl (+/-)-tetrahydrofuran-2-carboxylate

Downstream raw materials:

3-(2',6'-dimethoxy-biphenyl-4-yl)-2-{[2-(2-methoxy-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid tert-butyl ester

3-(2',6'-dimethoxy-biphenyl-4-yl)-2-{[2-(2-hydroxy-ethyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid tert-butyl ester

2-({2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-furan-2-carbonyl}-amino)-3-(2',6'-dimethoxy-biphenyl-4-yl)-propionic acid tert-butyl ester