(2R,3S,6S)-3-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-N-methoxy-2,6-N-trimethylheptanamide

Base Information

• Chemical Name: (2R,3S,6S)-3-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-N-methoxy-2,6-N-trimethylheptanamide
• CAS No.: 947696-77-7
• Molecular Formula: C₃₃H₅₅NO₄Si₂
• Molecular Weight: 585.975
• Mol file: 947696-77-7.mol

Synonyms:(2R,3S,6S)-3-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-N-methoxy-2,6-N-trimethylheptanamide

Chemical Property of (2R,3S,6S)-3-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-N-methoxy-2,6-N-trimethylheptanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6S)-3-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-N-methoxy-2,6-N-trimethylheptanamide

There total 6 articles about (2R,3S,6S)-3-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-N-methoxy-2,6-N-trimethylheptanamide 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: 92.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide (947696-76-6) → (2R,3S,6S)-3-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-N-methoxy-2,6-N-trimethylheptanamide (947696-77-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.08.013 DOI:10.1002/chem.200700342

Reference yield:

(S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-pentanol (371784-89-3) → (2R,3S,6S)-3-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-N-methoxy-2,6-N-trimethylheptanamide (947696-77-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / 0 °C

2.1: Et₃N / 0 °C

2.2: 2.5 h / 0 °C

3.1: 79 percent / AlMe₃ / tetrahydrofuran / 3 h / 20 °C

4.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; oxalyl dichloride; trimethylaluminum; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation / 2.1: Evans asymmetric aldolization;

DOI:10.1016/j.tetlet.2004.08.013

Reference yield:

(4R,5S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,8-dimethyl-1-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-nonane-1,3-dione → (2R,3S,6S)-3-(tert-butyldimethylsilyloxy)-7-(tert-butyldiphenylsilyloxy)-N-methoxy-2,6-N-trimethylheptanamide (947696-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / AlMe₃ / tetrahydrofuran / 3 h / 20 °C

2: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; trimethylaluminum; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2004.08.013

upstream raw materials:

t-butyldimethylsiyl triflate

(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-2,6-N-trimethylheptanamide

(4R,5S)-4-methyl-5-phenyl-3-[(2R,3S,6S)-7-(tert-butyldiphenylsilyloxy)-3-hydroxy-2,6-dimethylheptanoyl]-1,3-oxazolidin-2-one

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

Downstream raw materials:

(4S)-4-benzyl-3-[(2S,3R,4S,5S,8S)-5-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,4,8-trimethylnonanoyl]-1,3-oxazolidin-2-one

(4S)-4-benzyl-3-[(2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,4,8-trimethylnonanoyl]-1,3-oxazolidin-2-one

(3S,4R,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-one

(2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-3,5,9-trimethyldecan-2-ol