(2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-ol

Base Information

Chemical Name:(2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-ol
CAS No.:162991-28-8
Molecular Formula:C₃₀H₄₀O₇
Molecular Weight:512.643
Hs Code.:

Synonyms:(2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-ol

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Chemical Property of (2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-ol

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Technology Process of (2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-ol

There total 14 articles about (2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-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:

: 162879-42-7
(2S,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-vinyl-1,6-dioxa-spiro[4.5]decan-9-ol

: 162991-28-8
(2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-ol

: (2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(S)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-ol

Guidance literature:: With dihydrogen peroxide; potassium hydrogencarbonate; benzonitrile; In methanol; at 0 ℃;
DOI:10.1021/ja992134m

Reference yield:

: 137664-71-2
2-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-methyl-propan-1-ol

: 162991-28-8
(2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

2.1: BF₃*Et₂O / CH₂Cl₂ / 0 °C

3.1: 85 percent / TsOH / dimethylformamide

4.1: n-BuLi; HMPA / tetrahydrofuran

4.2: 81 percent / DMPU / tetrahydrofuran / -20 °C

5.1: 95 percent / 2,6-lutidine

6.1: 94 percent / DIBAL / CH₂Cl₂ / -78 - 0 °C

7.1: 87 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

8.1: tetrahydrofuran / -78 °C

9.1: 95 percent / TBAF / 60 °C

10.1: 76 percent / HgCl₂; CaCO₃ / tetrahydrofuran

11.1: 30 percent aq. H₂O₂; PhCN; KHCO₃ / methanol / 0 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; benzonitrile; triethylamine; calcium carbonate; mercury dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Oxidation / 2.1: thioacetalization; deacetalization / 3.1: acetalization / 4.1: Metallation / 4.2: Addition / 5.1: silylation / 6.1: reductive cleavage / 7.1: Oxidation / 8.1: Grignard reaction / 9.1: desilylation / 10.1: Cyclization / 11.1: Epoxidation;
DOI:10.1021/ja992134m

Reference yield:

: 137664-74-5
(3R,4S)-1-Benzyloxy-4-(R)-oxiranyl-pentan-3-ol

: 162991-28-8
(2R,3S,5S,7R,8R,9S)-7-(2-Benzyloxy-ethyl)-3-(4-methoxy-benzyloxy)-4,4,8-trimethyl-2-(R)-oxiranyl-1,6-dioxa-spiro[4.5]decan-9-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / TMEDA / dimethylformamide

2.1: n-BuLi; HMPA / tetrahydrofuran

2.2: 81 percent / DMPU / tetrahydrofuran / -20 °C

3.1: 95 percent / 2,6-lutidine

4.1: 94 percent / DIBAL / CH₂Cl₂ / -78 - 0 °C

5.1: 87 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂

6.1: tetrahydrofuran / -78 °C

7.1: 95 percent / TBAF / 60 °C

8.1: 76 percent / HgCl₂; CaCO₃ / tetrahydrofuran

9.1: 30 percent aq. H₂O₂; PhCN; KHCO₃ / methanol / 0 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; pyridine-SO₃ complex; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; potassium hydrogencarbonate; dimethyl sulfoxide; benzonitrile; triethylamine; calcium carbonate; mercury dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Metallation / 2.2: Addition / 3.1: silylation / 4.1: reductive cleavage / 5.1: Oxidation / 6.1: Grignard reaction / 7.1: desilylation / 8.1: Cyclization / 9.1: Epoxidation;
DOI:10.1021/ja992134m