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

Base Information

• Chemical Name: (1R,4S,8R,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-8-(hydroxymethyl)-5,10-dioxatricyclo[6.2.1.0^4,9]undecan-2-one
• CAS No.: 914093-15-5
• Molecular Formula: C₂₇H₃₄O₅Si
• Molecular Weight: 466.649

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

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

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

There total 1 articles about (1R,4S,8R,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-8-(hydroxymethyl)-5,10-dioxatricyclo[6.2.1.0^4,9]undecan-2-one 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: 91.0%

(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) → (1R,4S,8R,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-8-(hydroxymethyl)-5,10-dioxatricyclo[6.2.1.04,9]undecan-2-one (914093-15-5)

Guidance literature:

With pyridine; ammonium cerium(IV) nitrate; In acetonitrile; for 2h; cooling;

DOI:10.1002/anie.200602030

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-(hydroxymethyl)-5,10-dioxatricyclo[6.2.1.04,9]undecan-2-one (914093-15-5) → (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 8 steps

1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

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

3: 53 mg / diethyl ether / 0.5 h / cooling

4: 93 percent / acetic acid / tetrahydrofuran / 20 h / 0 - 20 °C

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

6: 58 percent / trimethylsilyl triflate; molecular sieves 3 Angstroem / CH₂Cl₂ / 0.5 h / cooling

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

8: 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; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl alcohol; 6: Mukaiyama aldol reaction;

DOI:10.1002/anie.200602030

upstream raw materials:

(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:

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

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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