(1S,2S,3S,4R)-1-acetoxy-8-benzyloxy-2,3-epoxy-4-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene

Base Information

Chemical Name:(1S,2S,3S,4R)-1-acetoxy-8-benzyloxy-2,3-epoxy-4-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene
CAS No.:794575-13-6
Molecular Formula:C₂₅H₃₂O₅Si
Molecular Weight:440.612
Hs Code.:

Synonyms:(1S,2S,3S,4R)-1-acetoxy-8-benzyloxy-2,3-epoxy-4-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2S,3S,4R)-1-acetoxy-8-benzyloxy-2,3-epoxy-4-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene

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Technology Process of (1S,2S,3S,4R)-1-acetoxy-8-benzyloxy-2,3-epoxy-4-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene

There total 6 articles about (1S,2S,3S,4R)-1-acetoxy-8-benzyloxy-2,3-epoxy-4-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene 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: 75.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 794575-12-5
(1R,2R,3S,4S)-4-acetoxy-8-benzyloxy-2,3-epoxy-1,2,3,4-tetrahydronaphthalen-1-ol

: 794575-13-6
(1S,2S,3S,4R)-1-acetoxy-8-benzyloxy-2,3-epoxy-4-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene

Guidance literature:: With 1H-imidazole; In dichloromethane; for 1h;
DOI:10.1016/j.tetasy.2004.07.051

Reference yield:

: 481-39-0
5-hydroxynaphtho-1,4-quinone

: 794575-13-6
(1S,2S,3S,4R)-1-acetoxy-8-benzyloxy-2,3-epoxy-4-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene

Guidance literature:: Multi-step reaction with 5 steps

1: 65 percent / silver(II) oxide / CH₂Cl₂

2: 87 percent / hydrogen peroxide; potassium carbonate / H₂O; acetone / 2 h / 0 °C

3: 54 percent / K-selectride / tetrahydrofuran / 3 h / -78 - 20 °C

4: 30 percent / Burholderia cepacia lipase / 16 h / 50 °C

5: 75 percent / imidazole / CH₂Cl₂ / 1 h

With 1H-imidazole; silver(II) oxide; Burholderia cepacia lipase; dihydrogen peroxide; potassium tri-sec-butyl-borohydride; potassium carbonate; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1016/j.tetasy.2004.07.051

Reference yield:

: 75445-61-3
5-(benzyloxy)-1,4-dihydronaphthalene-1,4-dione

: 794575-13-6
(1S,2S,3S,4R)-1-acetoxy-8-benzyloxy-2,3-epoxy-4-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / hydrogen peroxide; potassium carbonate / H₂O; acetone / 2 h / 0 °C

2: 54 percent / K-selectride / tetrahydrofuran / 3 h / -78 - 20 °C

3: 30 percent / Burholderia cepacia lipase / 16 h / 50 °C

4: 75 percent / imidazole / CH₂Cl₂ / 1 h

With 1H-imidazole; Burholderia cepacia lipase; dihydrogen peroxide; potassium tri-sec-butyl-borohydride; potassium carbonate; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1016/j.tetasy.2004.07.051