9-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5,10-dioxa-tricyclo[6.2.1.0^4,9]undecane-8-carbaldehyde

Base Information

• Chemical Name: 9-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5,10-dioxa-tricyclo[6.2.1.0^4,9]undecane-8-carbaldehyde
• CAS No.: 914093-24-6
• Molecular Formula: C₂₇H₃₂O₅Si
• Molecular Weight: 464.634

Synonyms:9-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5,10-dioxa-tricyclo[6.2.1.0^4,9]undecane-8-carbaldehyde

Chemical Property of 9-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5,10-dioxa-tricyclo[6.2.1.0^4,9]undecane-8-carbaldehyde

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of 9-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5,10-dioxa-tricyclo[6.2.1.0^4,9]undecane-8-carbaldehyde

There total 2 articles about 9-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5,10-dioxa-tricyclo[6.2.1.0^4,9]undecane-8-carbaldehyde 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: 92.0%

(1R,4S,8R,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-8-(hydroxymethyl)-5,10-dioxatricyclo[6.2.1.04,9]undecan-2-one (914093-15-5) → 9-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5,10-dioxa-tricyclo[6.2.1.04,9]undecane-8-carbaldehyde (914093-24-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 2h;

DOI:10.1002/anie.200602030

Reference yield:

(1R,4S,8R,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-8-[(4-methoxyphenoxy)methyl]-5,10-dioxatricyclo[6.2.1.04,9]undecan-2-one (914093-04-2) → 9-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5,10-dioxa-tricyclo[6.2.1.04,9]undecane-8-carbaldehyde (914093-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / ammonium cerium(IV) nitrate; pyridine / acetonitrile / 2 h / cooling

2: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

With pyridine; ammonium cerium(IV) nitrate; Dess-Martin periodane; In dichloromethane; acetonitrile;

DOI:10.1002/anie.200602030

Reference yield:

9-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5,10-dioxa-tricyclo[6.2.1.04,9]undecane-8-carbaldehyde (914093-24-6) → (1R,4S,8S,12R)-3-(4-hydroxy-3-methoxybenzylidene)-5,10,13-trioxatetracyclo[6.5.1.04,12.08,12]tetradecane-2,9-dione

Guidance literature:

Multi-step reaction with 7 steps

1: 68 mg / 2-methyl-2-butene; NaH₂PO₄; NaClO₄ / 2-methyl-propan-2-ol / 6 h

2: 53 mg / diethyl ether / 0.5 h / cooling

3: 93 percent / acetic acid / tetrahydrofuran / 20 h / 0 - 20 °C

4: 90 percent / triethylamine / CH₂Cl₂ / 5 h / cooling

5: 58 percent / trimethylsilyl triflate; molecular sieves 3 Angstroem / CH₂Cl₂ / 0.5 h / cooling

6: 9.7 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.17 h

7: 6.7 mg / NaHCO₃ / methanol / 24 h

With sodium dihydrogenphosphate; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium perchlorate; sodium hydrogencarbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl alcohol; 5: Mukaiyama aldol reaction;

DOI:10.1002/anie.200602030

upstream raw materials:

(1R,4S,8R,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-8-(hydroxymethyl)-5,10-dioxatricyclo[6.2.1.0^4,9]undecan-2-one

(1R,4S,8R,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-8-[(4-methoxyphenoxy)methyl]-5,10-dioxatricyclo[6.2.1.0^4,9]undecan-2-one

Downstream raw materials:

methyl (1R,4S,8S,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-2-oxo-5,10-dioxatricyclo[6.2.1.0^4,9]undecane-8-carboxylate

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