2-benzyloxy-6-methyldodecahydro-4,8,12-trioxadibenzo[a,d]cyclooctene-3,5-diol

Base Information

Chemical Name:2-benzyloxy-6-methyldodecahydro-4,8,12-trioxadibenzo[a,d]cyclooctene-3,5-diol
CAS No.:272787-73-2
Molecular Formula:C₂₁H₃₀O₆
Molecular Weight:378.466
Hs Code.:

Synonyms:2-benzyloxy-6-methyldodecahydro-4,8,12-trioxadibenzo[a,d]cyclooctene-3,5-diol

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Chemical Property of 2-benzyloxy-6-methyldodecahydro-4,8,12-trioxadibenzo[a,d]cyclooctene-3,5-diol

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Technology Process of 2-benzyloxy-6-methyldodecahydro-4,8,12-trioxadibenzo[a,d]cyclooctene-3,5-diol

There total 9 articles about 2-benzyloxy-6-methyldodecahydro-4,8,12-trioxadibenzo[a,d]cyclooctene-3,5-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: 98.0%

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

: 272787-73-2
2-benzyloxy-6-methyldodecahydro-4,8,12-trioxadibenzo[a,d]cyclooctene-3,5-diol

Guidance literature:: With water; acetic acid; at 20 ℃;
DOI:10.1055/s-2000-6507

Reference yield:

: 272787-72-1
(S)-2-Benzyloxy-3-((3aR,4R,5aS,9aR,11S,11aS)-2,2,11-trimethyl-decahydro-1,3,5,9-tetraoxa-benzo[a]cyclopenta[e]cycloocten-4-yl)-propan-1-ol

: 272787-73-2
2-benzyloxy-6-methyldodecahydro-4,8,12-trioxadibenzo[a,d]cyclooctene-3,5-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / Et₃N; SO₃*Py / dimethylsulfoxide / 0.17 h / 20 °C

2: 98 percent / 80 percent aq. AcOH / 20 °C

With pyridine-SO₃ complex; acetic acid; triethylamine; In dimethyl sulfoxide; 1: Oxidation / 2: Hydrolysis;
DOI:10.1016/S0040-4020(00)00467-1

Reference yield:

: acetic acid 1-(tert-butyldiphenylsilyloxymethyl)-2-(9-methyl-2,3,4,4a,6,9,10,10a-octahydro-1,5-dioxabenzocycloocten-6-yl)ethyl ester

: 272787-73-2
2-benzyloxy-6-methyldodecahydro-4,8,12-trioxadibenzo[a,d]cyclooctene-3,5-diol

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / K₂CO₃ / methanol / 2 h / 20 °C

2: 82 percent / NaH / dimethylformamide / -40 - 20 °C

3: 80 percent / NMO; OsO₄ / acetone; H₂O / 20 °C

4: 93 percent / TsOH*H₂O / 0.33 h / 20 °C

5: 96 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

6: 100 percent / Et₃N; SO₃*Py / dimethylsulfoxide / 0.17 h / 20 °C

7: 98 percent / 80 percent aq. AcOH / 20 °C

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