(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

Base Information

Chemical Name:(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
CAS No.:272787-72-1
Molecular Formula:C₂₄H₃₆O₆
Molecular Weight:420.546
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 96.0%

: 272787-71-0
[2-benzyloxy-3-(2,2,11-trimethyldecahydro-1,3,5,9-tetraoxabenzo[a]cyclopenta[e]cycloocten-4-yl)propoxy]-tert-butyldiphenyl silane

: 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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
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

: 272787-72-1
(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

Guidance literature:: Multi-step reaction with 4 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

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

: 272787-72-1
(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

Guidance literature:: Multi-step reaction with 5 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

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