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

Base Information

• Chemical Name: methyl (1R,4S,8S,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-2-oxo-5,10-dioxatricyclo[6.2.1.0^4,9]undecane-8-carboxylate
• CAS No.: 914093-16-6
• Molecular Formula: C₂₈H₃₄O₆Si
• Molecular Weight: 494.66

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

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

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

9-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-5,10-dioxa-tricyclo[6.2.1.04,9]undecane-8-carbaldehyde (914093-24-6) → methyl (1R,4S,8S,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-2-oxo-5,10-dioxatricyclo[6.2.1.04,9]undecane-8-carboxylate (914093-16-6)

Guidance literature:

Multi-step reaction with 2 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

With sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium perchlorate; In diethyl ether; tert-butyl alcohol;

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) → methyl (1R,4S,8S,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-2-oxo-5,10-dioxatricyclo[6.2.1.04,9]undecane-8-carboxylate (914093-16-6)

Guidance literature:

Multi-step reaction with 3 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

With sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium perchlorate; Dess-Martin periodane; In diethyl ether; dichloromethane; tert-butyl alcohol;

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) → methyl (1R,4S,8S,9R)-9-[(tert-butyldiphenylsilyl)oxymethyl]-2-oxo-5,10-dioxatricyclo[6.2.1.04,9]undecane-8-carboxylate (914093-16-6)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 68 mg / 2-methyl-2-butene; NaH₂PO₄; NaClO₄ / 2-methyl-propan-2-ol / 6 h

4: 53 mg / diethyl ether / 0.5 h / cooling

With pyridine; sodium dihydrogenphosphate; 2-methyl-but-2-ene; ammonium cerium(IV) nitrate; sodium perchlorate; Dess-Martin periodane; In diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol;

DOI:10.1002/anie.200602030

upstream raw materials:

diazomethane

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

(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

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