(+)-(1β,11α,12α,16β)-20-(tert-butyldiphenylsiloxy)-12-(acetyloxy)-16-methoxypicrasane-1,11-diol

Base Information

Chemical Name:(+)-(1β,11α,12α,16β)-20-(tert-butyldiphenylsiloxy)-12-(acetyloxy)-16-methoxypicrasane-1,11-diol
CAS No.:149400-20-4
Molecular Formula:C₃₉H₅₆O₇Si
Molecular Weight:664.955
Hs Code.:

Synonyms:(+)-(1β,11α,12α,16β)-20-(tert-butyldiphenylsiloxy)-12-(acetyloxy)-16-methoxypicrasane-1,11-diol

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Chemical Property of (+)-(1β,11α,12α,16β)-20-(tert-butyldiphenylsiloxy)-12-(acetyloxy)-16-methoxypicrasane-1,11-diol

Chemical Property:

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Technology Process of (+)-(1β,11α,12α,16β)-20-(tert-butyldiphenylsiloxy)-12-(acetyloxy)-16-methoxypicrasane-1,11-diol

There total 22 articles about (+)-(1β,11α,12α,16β)-20-(tert-butyldiphenylsiloxy)-12-(acetyloxy)-16-methoxypicrasane-1,11-diol 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:

: 95421-98-0
(E)-4-methyl-3,5-hexadienoic acid

: 130575-38-1,149400-20-4
Acetic acid (1R,2S,3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bS,11cR)-11c-(tert-butyl-diphenyl-silanyloxymethyl)-1,11-dihydroxy-5-methoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-yl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 72 percent / LiClO₄ / diethyl ether / 9 h / Ambient temperature

2: 1.) NaBH₄, 2.) concd. HCl / 1.) methanol, 0 deg C

3: 86 percent / imidazole / dimethylformamide

4: 100 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

5: 100 percent / concd. HCl / tetrahydrofuran

6: 1.) B₂H₆, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C

7: PCC, NaOAc / CH₂Cl₂

8: 1.) LDA / 1.) THF, from -78 deg C to 0 deg C, 2.) -78 deg C

9: Pd(OAc)2, Na₂CO₃ / acetonitrile / 45 °C

10: 81 percent / lithium, liquid ammonia, tert-butyl alcohol / -78 °C

11: methanol; tetrahydrofuran

12: n-butyllithium / -78 °C

14: 100 percent / Et₃N, DMAP / CH₂Cl₂

15: 83 percent / OsO₄, pyridine

With pyridine; 1H-imidazole; hydrogenchloride; dmap; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; lithium; diisobutylaluminium hydride; sodium carbonate; triethylamine; pyridinium chlorochromate; diborane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja00181a079

Reference yield:

: 86669-09-2,87758-23-4,123929-85-1
(4aR,5S,8S,8aR)-8-Methoxy-5,8a-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde

: 130575-38-1,149400-20-4
Acetic acid (1R,2S,3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bS,11cR)-11c-(tert-butyl-diphenyl-silanyloxymethyl)-1,11-dihydroxy-5-methoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-yl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 72 percent / LiClO₄ / diethyl ether / 9 h / Ambient temperature

2: 1.) NaBH₄, 2.) concd. HCl / 1.) methanol, 0 deg C

3: 86 percent / imidazole / dimethylformamide

4: 100 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

5: 100 percent / concd. HCl / tetrahydrofuran

6: 1.) B₂H₆, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C

7: PCC, NaOAc / CH₂Cl₂

8: 1.) LDA / 1.) THF, from -78 deg C to 0 deg C, 2.) -78 deg C

9: Pd(OAc)2, Na₂CO₃ / acetonitrile / 45 °C

10: 81 percent / lithium, liquid ammonia, tert-butyl alcohol / -78 °C

11: methanol; tetrahydrofuran

12: n-butyllithium / -78 °C

14: 100 percent / Et₃N, DMAP / CH₂Cl₂

15: 83 percent / OsO₄, pyridine

With pyridine; 1H-imidazole; hydrogenchloride; dmap; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; lithium; diisobutylaluminium hydride; sodium carbonate; triethylamine; pyridinium chlorochromate; diborane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja00181a079

Reference yield:

: (3S,3aS,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene-5,11-diol

: 149400-20-4
(+)-(1β,11α,12α,16β)-20-(tert-butyldiphenylsiloxy)-12-(acetyloxy)-16-methoxypicrasane-1,11-diol

Guidance literature:: Multi-step reaction with 3 steps

1: pyridinium p-toluenesulfonate / tetrahydrofuran / 12 h

2: 100 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 45 min

3: 1.) pyridine, OsO₄, 2.) aq. sodium bisulfite / 1.) from 0 deg C to RT, 25.5 h, 2.) 24 h

With pyridine; dmap; osmium(VIII) oxide; pyridinium p-toluenesulfonate; sodium hydrogensulfite; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00067a025