[(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-methanol

Base Information

Chemical Name:[(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-methanol
CAS No.:349648-97-1
Molecular Formula:C₂₉H₄₄O₄Si₂
Molecular Weight:512.837
Hs Code.:

[(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-methanol

Synonyms:[(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-methanol

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Chemical Property of [(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-methanol

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Technology Process of [(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-methanol

There total 14 articles about [(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-methanol 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%

: 349648-96-0
(1R,2S,3R,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-ene

: 349648-97-1
[(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-methanol

Guidance literature:: With bromocatecholborane; potassium carbonate; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ja010643u

Reference yield:

: 349648-91-5
1S,5R-1-acetoxymethyl-5-hydromethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one

: 349648-97-1
[(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-methanol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

2.1: 95 percent / K₂CO₃ / methanol / 8 h / 20 °C

3.1: 97 percent / diisopropylethylamine / acetonitrile / 2 h / Heating

4.1: AIBN / benzene / 24 h / Heating

5.1: 75 percent / NaOMe / methanol

6.1: LiBr; methyllithium / tetrahydrofuran; diethyl ether / 0 - 20 °C

6.2: tetrahydrofuran; diethyl ether / 0.33 h / -78 - 0 °C

7.1: 819 mg / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 71 percent / [o-O-C₆H₄-O]BBr; K₂CO₃ / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; 1H-imidazole; bromocatecholborane; methyllithium; sodium methylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; lithium bromide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ja010643u

Reference yield:

: (1R*,5S*)-1,5-bis(hydroxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

: 349648-97-1
[(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-methanol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 14.5 g / pyridine; DMAP / CH₂Cl₂ / 8 h / 0 °C

2.1: lipase from Candida rugosa / 24 h / 20 °C / pH 7

3.1: 98 percent / imidazole / CH₂Cl₂ / 8 h / 20 °C

4.1: 95 percent / K₂CO₃ / methanol / 8 h / 20 °C

5.1: 97 percent / diisopropylethylamine / acetonitrile / 2 h / Heating

6.1: AIBN / benzene / 24 h / Heating

7.1: 75 percent / NaOMe / methanol

8.1: LiBr; methyllithium / tetrahydrofuran; diethyl ether / 0 - 20 °C

8.2: tetrahydrofuran; diethyl ether / 0.33 h / -78 - 0 °C

9.1: 819 mg / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 71 percent / [o-O-C₆H₄-O]BBr; K₂CO₃ / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; 1H-imidazole; dmap; lipase from Candida rugosa; bromocatecholborane; methyllithium; sodium methylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; lithium bromide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ja010643u