Technology Process of Acetic acid (2S,3S,3aR,4S,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-butyl-diphenyl-silanyloxymethyl)-2,11-dihydroxy-3,8,11a-trimethyl-1,5,10-trioxo-1,2,3,3a,4,5,6a,7,7a,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-4-yl ester
There total 11 articles about Acetic acid (2S,3S,3aR,4S,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-butyl-diphenyl-silanyloxymethyl)-2,11-dihydroxy-3,8,11a-trimethyl-1,5,10-trioxo-1,2,3,3a,4,5,6a,7,7a,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-4-yl ester which
guide to synthetic route it.
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synthetic route:
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141762-93-8
Acetic acid (2S,3S,3aR,4S,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-butyl-diphenyl-silanyloxymethyl)-2,11-dihydroxy-3,8,11a-trimethyl-1,5,10-trioxo-1,2,3,3a,4,5,6a,7,7a,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-4-yl ester
- Guidance literature:
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With
boron tribromide;
In
dichloromethane;
1) -78 deg C, 1 h, 2) -43 deg C, 1.5 h;
DOI:10.1016/S0040-4039(00)74149-9
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130575-40-5,149400-23-7
(2S,3S,3aR,5R,6aS,7aR,8S,10R,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-10-hydroxy-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-1-one
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141762-93-8
Acetic acid (2S,3S,3aR,4S,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-butyl-diphenyl-silanyloxymethyl)-2,11-dihydroxy-3,8,11a-trimethyl-1,5,10-trioxo-1,2,3,3a,4,5,6a,7,7a,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-4-yl ester
- Guidance literature:
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Multi-step reaction with 11 steps
1: Dess-Martin periodinane reagent / CH2Cl2 / 1 h
2: 10percent HCl / tetrahydrofuran / 24 h
3: POCl3, pyridine / 1 h / 80 °C
4: 1) OsO4, 2) NaHSO3 / 1) pyridine, 0 deg C, 1 h, 2) 2 h
5: 75 percent / Dess-Martin periodinane reagent / CH2Cl2 / 1.5 h
6: 82 percent / NEt3, DMAP / CH2Cl2
7: 1) LiHMDS, TMSCl, 2) NBS / 1) THF, -78 deg C to rt
8: 93 percent / Li2CO3, LiBr / dimethylformamide / 0.75 h / 120 °C
9: 10percent HCl / tetrahydrofuran / 0.5 h
10: DMAP, pyridine / CH2Cl2
11: 46 percent / BBr3 / CH2Cl2 / 1) -78 deg C, 1 h, 2) -43 deg C, 1.5 h
With
pyridine; hydrogenchloride; dmap; N-Bromosuccinimide; osmium(VIII) oxide; chloro-trimethyl-silane; boron tribromide; lithium carbonate; Dess-Martin periodane; sodium hydrogensulfite; triethylamine; lithium bromide; lithium hexamethyldisilazane; trichlorophosphate;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)74149-9
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141762-94-9,149400-47-5,149400-48-6
(2S,3S,3aR,5R,6aS,7aR,8S,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,10-dione
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141762-93-8
Acetic acid (2S,3S,3aR,4S,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-butyl-diphenyl-silanyloxymethyl)-2,11-dihydroxy-3,8,11a-trimethyl-1,5,10-trioxo-1,2,3,3a,4,5,6a,7,7a,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-4-yl ester
- Guidance literature:
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Multi-step reaction with 9 steps
1: POCl3, pyridine / 1 h / 80 °C
2: 1) OsO4, 2) NaHSO3 / 1) pyridine, 0 deg C, 1 h, 2) 2 h
3: 75 percent / Dess-Martin periodinane reagent / CH2Cl2 / 1.5 h
4: 82 percent / NEt3, DMAP / CH2Cl2
5: 1) LiHMDS, TMSCl, 2) NBS / 1) THF, -78 deg C to rt
6: 93 percent / Li2CO3, LiBr / dimethylformamide / 0.75 h / 120 °C
7: 10percent HCl / tetrahydrofuran / 0.5 h
8: DMAP, pyridine / CH2Cl2
9: 46 percent / BBr3 / CH2Cl2 / 1) -78 deg C, 1 h, 2) -43 deg C, 1.5 h
With
pyridine; hydrogenchloride; dmap; N-Bromosuccinimide; osmium(VIII) oxide; chloro-trimethyl-silane; boron tribromide; lithium carbonate; Dess-Martin periodane; sodium hydrogensulfite; triethylamine; lithium bromide; lithium hexamethyldisilazane; trichlorophosphate;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)74149-9