(2R)-N-[(2R,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-2-(prop-2-ynyl)heptanoyl]bornane-10,2-sultam

Base Information

Chemical Name:(2R)-N-[(2R,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-2-(prop-2-ynyl)heptanoyl]bornane-10,2-sultam
CAS No.:398477-92-4
Molecular Formula:C₄₀H₆₇NO₇SSi₂
Molecular Weight:762.211
Hs Code.:

Synonyms:(2R)-N-[(2R,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-2-(prop-2-ynyl)heptanoyl]bornane-10,2-sultam

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Chemical Property of (2R)-N-[(2R,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-2-(prop-2-ynyl)heptanoyl]bornane-10,2-sultam

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Technology Process of (2R)-N-[(2R,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-2-(prop-2-ynyl)heptanoyl]bornane-10,2-sultam

There total 5 articles about (2R)-N-[(2R,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-2-(prop-2-ynyl)heptanoyl]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: 90.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 398477-91-3
(2R)-N-[(2R,3S,5R)-7-(tert-butyldimethylsilyloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)heptanoyl]bornane-10,2-sultam

: 398477-92-4
(2R)-N-[(2R,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-2-(prop-2-ynyl)heptanoyl]bornane-10,2-sultam

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -10 - 20 ℃; for 4h;
DOI:10.1021/ja0177713

Reference yield:

: 89922-82-7
3-(tert-butyldimethylsilanyloxy)propionaldehyde

: 398477-92-4
(2R)-N-[(2R,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-2-(prop-2-ynyl)heptanoyl]bornane-10,2-sultam

Guidance literature:: Multi-step reaction with 5 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

3.1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 °C

4.2: 74 percent / CH₂Cl₂ / 2 h / -78 °C

5.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -10 - 20 °C

With 2,6-dimethylpyridine; trifluorormethanesulfonic acid; titanium tetrachloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In diethyl ether; dichloromethane;
DOI:10.1021/ja0177713

Reference yield:

: 251641-42-6
(R)-5-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)pentanal

: 398477-92-4
(2R)-N-[(2R,3S,5R)-3,7-bis-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-2-(prop-2-ynyl)heptanoyl]bornane-10,2-sultam

Guidance literature:: Multi-step reaction with 2 steps

1.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 °C

1.2: 74 percent / CH₂Cl₂ / 2 h / -78 °C

2.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -10 - 20 °C

With 2,6-dimethylpyridine; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ja0177713