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

Base Information

Chemical Name:(S)-2-Benzyloxy-3-((3aS,4R,5aS,9aR,11S,11aR)-2,2,11-trimethyl-decahydro-1,3,5,9-tetraoxa-benzo[a]cyclopenta[e]cycloocten-4-yl)-propionaldehyde
CAS No.:300343-80-0
Molecular Formula:C₂₄H₃₄O₆
Molecular Weight:418.53
Hs Code.:

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

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Chemical Property of (S)-2-Benzyloxy-3-((3aS,4R,5aS,9aR,11S,11aR)-2,2,11-trimethyl-decahydro-1,3,5,9-tetraoxa-benzo[a]cyclopenta[e]cycloocten-4-yl)-propionaldehyde

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Technology Process of (S)-2-Benzyloxy-3-((3aS,4R,5aS,9aR,11S,11aR)-2,2,11-trimethyl-decahydro-1,3,5,9-tetraoxa-benzo[a]cyclopenta[e]cycloocten-4-yl)-propionaldehyde

There total 7 articles about (S)-2-Benzyloxy-3-((3aS,4R,5aS,9aR,11S,11aR)-2,2,11-trimethyl-decahydro-1,3,5,9-tetraoxa-benzo[a]cyclopenta[e]cycloocten-4-yl)-propionaldehyde 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: 89.0%

: 300343-79-7
(S)-2-Benzyloxy-3-((3aS,4R,5aS,9aR,11S,11aR)-2,2,11-trimethyl-decahydro-1,3,5,9-tetraoxa-benzo[a]cyclopenta[e]cycloocten-4-yl)-propan-1-ol

: 300343-80-0
(S)-2-Benzyloxy-3-((3aS,4R,5aS,9aR,11S,11aR)-2,2,11-trimethyl-decahydro-1,3,5,9-tetraoxa-benzo[a]cyclopenta[e]cycloocten-4-yl)-propionaldehyde

Guidance literature:: With pyridine-SO₃ complex; triethylamine; In dimethyl sulfoxide;
DOI:10.1016/S0040-4020(00)00467-1

Reference yield:

: 100-39-0
benzyl bromide

: 300343-80-0
(S)-2-Benzyloxy-3-((3aS,4R,5aS,9aR,11S,11aR)-2,2,11-trimethyl-decahydro-1,3,5,9-tetraoxa-benzo[a]cyclopenta[e]cycloocten-4-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 5 steps

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

2: 7 percent / NMO; OsO₄ / acetone; H₂O / 20 °C

3: 93 percent / TsOH / 20 °C

4: 89 percent / TBAF / tetrahydrofuran / 20 °C

5: 89 percent / SO₃*Py; Et₃N / dimethylsulfoxide

With osmium(VIII) oxide; N-methyl-2-indolinone; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1: Alkylation / 2: Oxidation / 3: Cyclization / 4: desilylation / 5: Oxidation;
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

: 300343-80-0
(S)-2-Benzyloxy-3-((3aS,4R,5aS,9aR,11S,11aR)-2,2,11-trimethyl-decahydro-1,3,5,9-tetraoxa-benzo[a]cyclopenta[e]cycloocten-4-yl)-propionaldehyde

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: 7 percent / NMO; OsO₄ / acetone; H₂O / 20 °C

4: 93 percent / TsOH / 20 °C

5: 89 percent / TBAF / tetrahydrofuran / 20 °C

6: 89 percent / SO₃*Py; Et₃N / dimethylsulfoxide

With osmium(VIII) oxide; N-methyl-2-indolinone; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; toluene-4-sulfonic 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;
DOI:10.1016/S0040-4020(00)00467-1