(2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)pentanoyl]bornane-10,2-sultam

Base Information

• Chemical Name: (2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)pentanoyl]bornane-10,2-sultam
• CAS No.: 398477-90-2
• Molecular Formula: C₂₉H₄₇NO₆SSi
• Molecular Weight: 565.847
• Mol file: 398477-90-2.mol

Synonyms:(2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)pentanoyl]bornane-10,2-sultam

Chemical Property of (2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)pentanoyl]bornane-10,2-sultam

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)pentanoyl]bornane-10,2-sultam

There total 3 articles about (2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)pentanoyl]bornane-10,2-sultam 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: 72.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + (2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-hydroxypentanoyl]-bornane-10,2-sultam (398477-89-9) → (2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)pentanoyl]bornane-10,2-sultam (398477-90-2)

Guidance literature:

With trifluorormethanesulfonic acid; In diethyl ether; at 20 ℃; for 2h;

DOI:10.1021/ja0177713

Reference yield:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → (2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)pentanoyl]bornane-10,2-sultam (398477-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.5 h / -5 °C

1.2: 66 percent / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 72 percent / TfOH / diethyl ether / 2 h / 20 °C

With trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In diethyl ether; dichloromethane;

DOI:10.1021/ja0177713

Reference yield:

1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.01.5]dec-4-yl]-ethanone (141993-16-0) → (2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)pentanoyl]bornane-10,2-sultam (398477-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.5 h / -5 °C

1.2: 66 percent / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 72 percent / TfOH / diethyl ether / 2 h / 20 °C

With trifluorormethanesulfonic acid; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In diethyl ether; dichloromethane;

DOI:10.1021/ja0177713

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

(2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-hydroxypentanoyl]-bornane-10,2-sultam

3-(tert-butyldimethylsilanyloxy)propionaldehyde

1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.0^1.5]dec-4-yl]-ethanone

Downstream raw materials:

(R)-5-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)pentanal

(4R,5S,7R)-5,9-bis-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-4-methylnon-1-ene

(4R,5S,7R)-5,9-bis-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-4-methylnon-1-yne

(2S,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptan-1-ol