(2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-N-methoxy-2,4,8-N-tetramethylnonanamide

Base Information

• Chemical Name: (2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-N-methoxy-2,4,8-N-tetramethylnonanamide
• CAS No.: 947696-80-2
• Molecular Formula: C₄₂H₇₅NO₅Si₃
• Molecular Weight: 758.318
• Mol file: 947696-80-2.mol

Synonyms:

Chemical Property of (2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-N-methoxy-2,4,8-N-tetramethylnonanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-N-methoxy-2,4,8-N-tetramethylnonanamide

There total 14 articles about (2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-N-methoxy-2,4,8-N-tetramethylnonanamide 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:

N,0-dimethylhydroxylamine (1117-97-1) + (2S,3R,4R,5S,8S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-2,4,8-trimethyl-nonanoic acid → (2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-N-methoxy-2,4,8-N-tetramethylnonanamide (947696-80-2)

Guidance literature:

With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2004.08.013

Reference yield:

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (2S,3R,4R,5S,8S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-2,4,8-trimethyl-nonanoic acid → (2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-N-methoxy-2,4,8-N-tetramethylnonanamide (947696-80-2)

Guidance literature:

(2S,3R,4R,5S,8S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-2,4,8-trimethyl-nonanoic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 0 ℃; for 0.5h;

N,O-dimethylhydroxylamine*hydrochloride; In dichloromethane; at 20 ℃; Further stages.;

DOI:10.1002/chem.200700342

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-N-methoxy-2,4,8-N-tetramethylnonanamide (947696-80-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / 2.6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2.1: aq. H₂O₂; LiOH monohydrate / tetrahydrofuran / 0 - 20 °C

3.1: 1,1'-carbonyl-diimidazole / CH₂Cl₂ / 0.5 h / 0 °C

3.2: 2.49 g / CH₂Cl₂ / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; dihydrogen peroxide; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.200700342

upstream raw materials:

N,0-dimethylhydroxylamine

N,O-dimethylhydroxylamine*hydrochloride

(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

Downstream raw materials:

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

(2S,3R,4S,5R,6S,9S)-4,6-bis(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-3,5,9-trimethyldecane