imidazole-1-carbothioic acid O-(2-benzyloxy-6-methyl-3-oxo-dodecahydro-4,8,12-trioxadibenzo[a,d]cycloocten-5-yl) ester

Base Information

Chemical Name:imidazole-1-carbothioic acid O-(2-benzyloxy-6-methyl-3-oxo-dodecahydro-4,8,12-trioxadibenzo[a,d]cycloocten-5-yl) ester
CAS No.:272787-62-9
Molecular Formula:C₂₅H₃₀N₂O₆S
Molecular Weight:486.589
Hs Code.:

Synonyms:imidazole-1-carbothioic acid O-(2-benzyloxy-6-methyl-3-oxo-dodecahydro-4,8,12-trioxadibenzo[a,d]cycloocten-5-yl) ester

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Chemical Property of imidazole-1-carbothioic acid O-(2-benzyloxy-6-methyl-3-oxo-dodecahydro-4,8,12-trioxadibenzo[a,d]cycloocten-5-yl) ester

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Technology Process of imidazole-1-carbothioic acid O-(2-benzyloxy-6-methyl-3-oxo-dodecahydro-4,8,12-trioxadibenzo[a,d]cycloocten-5-yl) ester

There total 11 articles about imidazole-1-carbothioic acid O-(2-benzyloxy-6-methyl-3-oxo-dodecahydro-4,8,12-trioxadibenzo[a,d]cycloocten-5-yl) ester 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: 77.0%

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 272787-61-8
2-benzyloxy-5-hydroxy-6-methyldodecahydro-4,8,12-trioxadibenzo[a,d]cyclooctene-3-one

: 272787-62-9
imidazole-1-carbothioic acid O-(2-benzyloxy-6-methyl-3-oxo-dodecahydro-4,8,12-trioxadibenzo[a,d]cycloocten-5-yl) ester

Guidance literature:: In 1,2-dichloro-ethane; Heating;
DOI:10.1055/s-2000-6507

Reference yield:

: 272787-60-7
2-benzyloxy-3-(2,2,11-trimethyldecahydro-1,3,5,9-tetraoxabenzo[a]cyclopenta[e]cycloocten-4-yl)propionaldehyde

: 272787-62-9
imidazole-1-carbothioic acid O-(2-benzyloxy-6-methyl-3-oxo-dodecahydro-4,8,12-trioxadibenzo[a,d]cycloocten-5-yl) ester

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / 80 percent aq. AcOH / 20 °C

2: 77 percent / Br₂; NaOAc / dimethylformamide / 0.5 h / 0 - 20 °C

3: 67 percent / CH₂Cl₂ / Heating

With bromine; sodium acetate; acetic acid; In dichloromethane; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Oxidation / 3: Esterification;
DOI:10.1016/S0040-4020(00)00467-1

Reference yield:

: (S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-((Z)-(4aS,6R,9S,10aR)-9-methyl-2,3,4,4a,6,9,10,10a-octahydro-1,5-dioxa-benzocycloocten-6-yl)-propan-2-ol

: 272787-62-9
imidazole-1-carbothioic acid O-(2-benzyloxy-6-methyl-3-oxo-dodecahydro-4,8,12-trioxadibenzo[a,d]cycloocten-5-yl) ester

Guidance literature:: Multi-step reaction with 8 steps

1: 82 percent / NaH / dimethylformamide / -40 - 20 °C

2: 80 percent / NMO; OsO₄ / acetone; H₂O / 20 °C

3: 93 percent / TsOH*H₂O / 0.33 h / 20 °C

4: 96 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

5: 100 percent / Et₃N; SO₃*Py / dimethylsulfoxide / 0.17 h / 20 °C

6: 98 percent / 80 percent aq. AcOH / 20 °C

7: 77 percent / Br₂; NaOAc / dimethylformamide / 0.5 h / 0 - 20 °C

8: 67 percent / CH₂Cl₂ / Heating

With osmium(VIII) oxide; N-methyl-2-indolinone; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; bromine; sodium acetate; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1: Alkylation / 2: Oxidation / 3: Cyclization / 4: desilylation / 5: Oxidation / 6: Hydrolysis / 7: Oxidation / 8: Esterification;
DOI:10.1016/S0040-4020(00)00467-1