(1R,4R)-11-(benzyloxy)-1-[(1R,4R,5R,8R,9R)-9-(tert-butyldimethylsilyloxy)-1,4:5,8-diepoxyhenycosanyl]-4-(methoxymethoxy)undec-2-yn-1-ol

Base Information

Chemical Name:(1R,4R)-11-(benzyloxy)-1-[(1R,4R,5R,8R,9R)-9-(tert-butyldimethylsilyloxy)-1,4:5,8-diepoxyhenycosanyl]-4-(methoxymethoxy)undec-2-yn-1-ol
CAS No.:887330-25-8
Molecular Formula:C₄₇H₈₂O₇Si
Molecular Weight:787.249
Hs Code.:

Synonyms:(1R,4R)-11-(benzyloxy)-1-[(1R,4R,5R,8R,9R)-9-(tert-butyldimethylsilyloxy)-1,4:5,8-diepoxyhenycosanyl]-4-(methoxymethoxy)undec-2-yn-1-ol

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Chemical Property of (1R,4R)-11-(benzyloxy)-1-[(1R,4R,5R,8R,9R)-9-(tert-butyldimethylsilyloxy)-1,4:5,8-diepoxyhenycosanyl]-4-(methoxymethoxy)undec-2-yn-1-ol

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Technology Process of (1R,4R)-11-(benzyloxy)-1-[(1R,4R,5R,8R,9R)-9-(tert-butyldimethylsilyloxy)-1,4:5,8-diepoxyhenycosanyl]-4-(methoxymethoxy)undec-2-yn-1-ol

There total 7 articles about (1R,4R)-11-(benzyloxy)-1-[(1R,4R,5R,8R,9R)-9-(tert-butyldimethylsilyloxy)-1,4:5,8-diepoxyhenycosanyl]-4-(methoxymethoxy)undec-2-yn-1-ol 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: 65.0%

: 887330-22-5
(3R)-10-(benzyloxy)-3-(methoxymethoxy)dec-1-yne

: 887330-24-7
(2R,5R,2'R,5'R)-5'-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-tridecyl]-octahydro-[2,2']bifuranyl-5-carbaldehyde

: 887330-25-8
(1R,4R)-11-(benzyloxy)-1-[(1R,4R,5R,8R,9R)-9-(tert-butyldimethylsilyloxy)-1,4:5,8-diepoxyhenycosanyl]-4-(methoxymethoxy)undec-2-yn-1-ol

Guidance literature:: With (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; for 6h;
DOI:10.1002/ejoc.200500850

Reference yield:

: 887330-20-3
10-(benzyloxy)dec-1-yn-3-one

: 887330-25-8
(1R,4R)-11-(benzyloxy)-1-[(1R,4R,5R,8R,9R)-9-(tert-butyldimethylsilyloxy)-1,4:5,8-diepoxyhenycosanyl]-4-(methoxymethoxy)undec-2-yn-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 60 percent / (R)-Alpine-Borane(R) / tetrahydrofuran / 6 h / 20 °C

2: 96 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

3: 65 percent / Zn(OTf)2; (1R,2S)-(-)-N-methylephedrine; Et₃N / toluene / 6 h / 20 °C

With B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/ejoc.200500850

Reference yield:

: 887330-19-0
rac-10-(benzyloxy)dec-1-yn-3-ol

: 887330-25-8
(1R,4R)-11-(benzyloxy)-1-[(1R,4R,5R,8R,9R)-9-(tert-butyldimethylsilyloxy)-1,4:5,8-diepoxyhenycosanyl]-4-(methoxymethoxy)undec-2-yn-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

2: 60 percent / (R)-Alpine-Borane(R) / tetrahydrofuran / 6 h / 20 °C

3: 96 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

4: 65 percent / Zn(OTf)2; (1R,2S)-(-)-N-methylephedrine; Et₃N / toluene / 6 h / 20 °C

With B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; (-)-N-methylephedrine; zinc trifluoromethanesulfonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/ejoc.200500850