Technology Process of (2R,3R,4S,4aR,7R,8R,9aR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2,3,4a,7,8,9a-hexahydro-4H-1,6,9-trioxa-10-thia-anthracen-5-one
There total 10 articles about (2R,3R,4S,4aR,7R,8R,9aR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2,3,4a,7,8,9a-hexahydro-4H-1,6,9-trioxa-10-thia-anthracen-5-one which
guide to synthetic route it.
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synthetic route:
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629652-50-2
(2R,3R,4S,4aR,7R,8R,9aR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2,3,4a,7,8,9a-hexahydro-4H-1,6,9-trioxa-10-thia-anthracen-5-one
- Guidance literature:
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With
pyridine; phthalimidesulfenyl chloride;
In
chloroform;
at 20 ℃;
for 3h;
DOI:10.1021/jo034556r
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629652-50-2
(2R,3R,4S,4aR,7R,8R,9aR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2,3,4a,7,8,9a-hexahydro-4H-1,6,9-trioxa-10-thia-anthracen-5-one
- Guidance literature:
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Multi-step reaction with 9 steps
1: 70 percent / pyridinium p-toluenesulfonate / acetonitrile / 4.5 h / 0 - 20 °C
2: 95 percent / 4-dimethylaminopyridine; imidazole / dimethylformamide / 3 h / 20 °C
3: 73 percent / DIBAL-H / CH2Cl2 / 2.33 h / -15 - 0 °C
4: 84 percent / t-BuOK / dimethylsulfoxide / 3 h / 20 °C
5: 59 percent / HCl / dioxane; H2O / 1.5 h / 20 °C
6: 93 percent / HF / dimethylformamide; H2O / 120 h / 20 °C
7: 89 percent / Ag2CO3/Celite(R) / benzene / 18 h / Heating
8: 68 percent / (CF3CO)2O; DMSO; Et3N / CH2Cl2 / -60 - 20 °C
9: 76 percent / phthalimidosulfenyl chloride; pyridine / CHCl3 / 3 h / 20 °C
With
pyridine; 1H-imidazole; hydrogenchloride; dmap; phthalimidesulfenyl chloride; Celite; hydrogen fluoride; potassium tert-butylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; silver carbonate; trifluoroacetic anhydride;
In
1,4-dioxane; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo034556r
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629652-50-2
(2R,3R,4S,4aR,7R,8R,9aR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2,3,4a,7,8,9a-hexahydro-4H-1,6,9-trioxa-10-thia-anthracen-5-one
- Guidance literature:
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Multi-step reaction with 6 steps
1: 84 percent / t-BuOK / dimethylsulfoxide / 3 h / 20 °C
2: 59 percent / HCl / dioxane; H2O / 1.5 h / 20 °C
3: 93 percent / HF / dimethylformamide; H2O / 120 h / 20 °C
4: 89 percent / Ag2CO3/Celite(R) / benzene / 18 h / Heating
5: 68 percent / (CF3CO)2O; DMSO; Et3N / CH2Cl2 / -60 - 20 °C
6: 76 percent / phthalimidosulfenyl chloride; pyridine / CHCl3 / 3 h / 20 °C
With
pyridine; hydrogenchloride; phthalimidesulfenyl chloride; Celite; hydrogen fluoride; potassium tert-butylate; dimethyl sulfoxide; triethylamine; silver carbonate; trifluoroacetic anhydride;
In
1,4-dioxane; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo034556r