Technology Process of Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester
There total 11 articles about Acetic acid (1S,2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2,6-bis-benzyloxymethoxy-4-(4-methoxy-benzyloxy)-cyclohexyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
Proton Sponge; tetrabutylammomium bromide;
In
acetonitrile;
rt to 55 deg C;
DOI:10.1021/jo980501r
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 56 percent / Bu2SnO, Bu4NBr / toluene / Heating
2: 83 percent / p-TsOH monohydrate / methanol / 2 h / Ambient temperature
3: 65 percent / DMAP, Et3N / dimethylformamide / Ambient temperature; overnight
4: 95 percent / NaH / dimethylformamide / 2 h / Ambient temperature
5: 42 percent / aq. H2SO4 / methanol; acetone / 1 h / Ambient temperature
6: (COCl)2, Et3N / dimethylsulfoxide; CH2Cl2 / 078 deg C to rt
7: K2CO3 / acetonitrile / Heating; overnight
8: 1.) Hg(OAc)2, 2.) NaCl / 1.) acetone, H2O, 45 min, 2.) rt, 24 h
9: 83 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 0.75 h / Ambient temperature
10: 57 percent / proton sponge, n-Bu4NBr / acetonitrile / rt to 55 deg C
With
dmap; oxalyl dichloride; Proton Sponge; sulfuric acid; mercury(II) diacetate; tetrabutylammomium bromide; sodium tris(acetoxy)borohydride; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; sodium chloride;
In
methanol; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/jo980501r
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 95 percent / NaH / dimethylformamide / 2 h / Ambient temperature
2: 42 percent / aq. H2SO4 / methanol; acetone / 1 h / Ambient temperature
3: (COCl)2, Et3N / dimethylsulfoxide; CH2Cl2 / 078 deg C to rt
4: K2CO3 / acetonitrile / Heating; overnight
5: 1.) Hg(OAc)2, 2.) NaCl / 1.) acetone, H2O, 45 min, 2.) rt, 24 h
6: 83 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 0.75 h / Ambient temperature
7: 57 percent / proton sponge, n-Bu4NBr / acetonitrile / rt to 55 deg C
With
oxalyl dichloride; Proton Sponge; sulfuric acid; mercury(II) diacetate; tetrabutylammomium bromide; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; triethylamine; sodium chloride;
In
methanol; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jo980501r
