(1β,2α,12α)-20-(tert-butyldiphenylsiloxy)-1,2,12-trihydroxypicrasane-11,16-dione

Base Information

Chemical Name:(1β,2α,12α)-20-(tert-butyldiphenylsiloxy)-1,2,12-trihydroxypicrasane-11,16-dione
CAS No.:137175-19-0
Molecular Formula:C₃₆H₄₈O₇Si
Molecular Weight:620.858
Hs Code.:

Synonyms:(1β,2α,12α)-20-(tert-butyldiphenylsiloxy)-1,2,12-trihydroxypicrasane-11,16-dione

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Chemical Property of (1β,2α,12α)-20-(tert-butyldiphenylsiloxy)-1,2,12-trihydroxypicrasane-11,16-dione

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Technology Process of (1β,2α,12α)-20-(tert-butyldiphenylsiloxy)-1,2,12-trihydroxypicrasane-11,16-dione

There total 7 articles about (1β,2α,12α)-20-(tert-butyldiphenylsiloxy)-1,2,12-trihydroxypicrasane-11,16-dione 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: 87.0%

: 137175-18-9
(1β,2α,12α)-20-(tert-butyldiphenylsiloxy)-1,2,12-trihydroxypicrasane-11,16-dione 1,2-carbonate

: 137175-19-0
(1β,2α,12α)-20-(tert-butyldiphenylsiloxy)-1,2,12-trihydroxypicrasane-11,16-dione

Guidance literature:: With potassium carbonate; In tetrahydrofuran; methanol; for 1h; Ambient temperature;
DOI:10.1021/jo00025a039

Reference yield:

: 130575-39-2
(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-dione

: 137175-19-0
(1β,2α,12α)-20-(tert-butyldiphenylsiloxy)-1,2,12-trihydroxypicrasane-11,16-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 1) lithium hexamethylsisilazide, 2) Et₃N / THF, 1) 1.1) -78 deg C, 30 min., 1.2) 0 deg C, 30 min., 2) 2.1) -78 deg C, 15 min., 2.2) 0 deg C, 15 min.

2: 1) diborane, 2) 3.0 N aq. NaOH, 30percent aq. H₂O₂ / THF, 1) 1.1) -23 deg C, 15 min., 1.2) 0 deg C, 30 min., 1.3) 15 min., 2) RT, 4 h

3: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1) 0 deg C, 12.5 h, 2) RT, 1.5 h

4: 10percent aq. HCl / tetrahydrofuran / 42.5 h / Ambient temperature

5: pyridinium chlorochromate, CH₃COONa, Celite / CH₂Cl₂ / 1) 0 deg C, 15 min., 2) RT, 1.25 h, 3) 5 h

6: 90 percent / iodotrimethylsilane / acetonitrile / 1) -23 deg C, 20 min., 2) 0 deg C, 20 min., 3) RT, 2.5 h

7: 87 percent / K₂CO₃ / methanol; tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; dmap; sodium hydroxide; trimethylsilyl iodide; Celite; dihydrogen peroxide; sodium acetate; potassium carbonate; triethylamine; pyridinium chlorochromate; diborane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo00025a039

Reference yield:

: 137175-16-7
(1β,2α,12α,16β)-20-(tert-butyldiphenylsiloxy)-1,2-dihydroxy-16-methoxy-12-(methoxymethoxy)picrasan-11-one

: 137175-19-0
(1β,2α,12α)-20-(tert-butyldiphenylsiloxy)-1,2,12-trihydroxypicrasane-11,16-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1) 0 deg C, 12.5 h, 2) RT, 1.5 h

2: 10percent aq. HCl / tetrahydrofuran / 42.5 h / Ambient temperature

3: pyridinium chlorochromate, CH₃COONa, Celite / CH₂Cl₂ / 1) 0 deg C, 15 min., 2) RT, 1.25 h, 3) 5 h

4: 90 percent / iodotrimethylsilane / acetonitrile / 1) -23 deg C, 20 min., 2) 0 deg C, 20 min., 3) RT, 2.5 h

5: 87 percent / K₂CO₃ / methanol; tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; dmap; trimethylsilyl iodide; Celite; sodium acetate; potassium carbonate; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo00025a039