(2R)-N-[(4Z)-{(1S)-3-(tert-butyldimethylsilyloxy)-1-hydroxyprop-1-yl]-8-benzyloxyocten-1-oyl}bornane-10,2-sultam

Base Information

Chemical Name:(2R)-N-[(4Z)-{(1S)-3-(tert-butyldimethylsilyloxy)-1-hydroxyprop-1-yl]-8-benzyloxyocten-1-oyl}bornane-10,2-sultam
CAS No.:763110-44-7
Molecular Formula:C₃₄H₅₅NO₆SSi
Molecular Weight:633.965
Hs Code.:

Synonyms:(2R)-N-[(4Z)-{(1S)-3-(tert-butyldimethylsilyloxy)-1-hydroxyprop-1-yl]-8-benzyloxyocten-1-oyl}bornane-10,2-sultam

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R)-N-[(4Z)-{(1S)-3-(tert-butyldimethylsilyloxy)-1-hydroxyprop-1-yl]-8-benzyloxyocten-1-oyl}bornane-10,2-sultam

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2R)-N-[(4Z)-{(1S)-3-(tert-butyldimethylsilyloxy)-1-hydroxyprop-1-yl]-8-benzyloxyocten-1-oyl}bornane-10,2-sultam

There total 9 articles about (2R)-N-[(4Z)-{(1S)-3-(tert-butyldimethylsilyloxy)-1-hydroxyprop-1-yl]-8-benzyloxyocten-1-oyl}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: 71.0%

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

: 763110-42-5
(2R)-N-[(4Z)-8-benzyloxyocten-1-oyl]bornane-10,2-sultam

: 763110-44-7
(2R)-N-[(4Z)-{(1S)-3-(tert-butyldimethylsilyloxy)-1-hydroxyprop-1-yl]-8-benzyloxyocten-1-oyl}bornane-10,2-sultam

Guidance literature:: With N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In dichloromethane;
DOI:10.1016/S0040-4039(99)01523-3

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 763110-44-7
(2R)-N-[(4Z)-{(1S)-3-(tert-butyldimethylsilyloxy)-1-hydroxyprop-1-yl]-8-benzyloxyocten-1-oyl}bornane-10,2-sultam

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

1.2: 65 percent / tetrahydrofuran / 1.5 h / -78 °C

2.1: 97 percent / aq. NaOH / tetrahydrofuran / 20 °C

3.1: oxalyl chloride / 3 h / 20 °C

4.1: n-BuLi / hexane; toluene / 2 h / 20 °C

4.2: 79 percent / hexane; toluene / 20 °C

5.1: Et₂BOTf; (i-Pr)2NEt / CH₂Cl₂; hexane / 0.5 h / cooling

5.2: 71 percent / CH₂Cl₂; hexane / 5 h / -78 °C

With sodium hydroxide; n-butyllithium; oxalyl dichloride; sodium hexamethyldisilazane; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1039/b406280a

Reference yield:

: 4541-14-4
4-benzyloxy-butan-1-ol

: 763110-44-7
(2R)-N-[(4Z)-{(1S)-3-(tert-butyldimethylsilyloxy)-1-hydroxyprop-1-yl]-8-benzyloxyocten-1-oyl}bornane-10,2-sultam

Guidance literature:: Multi-step reaction with 6 steps

1.1: 99 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 2 h / -78 °C

2.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

2.2: 65 percent / tetrahydrofuran / 1.5 h / -78 °C

3.1: 97 percent / aq. NaOH / tetrahydrofuran / 20 °C

4.1: oxalyl chloride / 3 h / 20 °C

5.1: n-BuLi / hexane; toluene / 2 h / 20 °C

5.2: 79 percent / hexane; toluene / 20 °C

6.1: Et₂BOTf; (i-Pr)2NEt / CH₂Cl₂; hexane / 0.5 h / cooling

6.2: 71 percent / CH₂Cl₂; hexane / 5 h / -78 °C

With sodium hydroxide; n-butyllithium; oxalyl dichloride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: Swern oxidation;
DOI:10.1039/b406280a