tert-butyl-[3-(1,4-dioxa-spiro[4.5]dec-2-yl)-3-(3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane

Base Information

• Chemical Name: tert-butyl-[3-(1,4-dioxa-spiro[4.5]dec-2-yl)-3-(3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane
• CAS No.: 935252-92-9
• Molecular Formula: C₃₀H₄₁IO₄Si
• Molecular Weight: 620.643

Synonyms:tert-butyl-[3-(1,4-dioxa-spiro[4.5]dec-2-yl)-3-(3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane

Chemical Property of tert-butyl-[3-(1,4-dioxa-spiro[4.5]dec-2-yl)-3-(3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of tert-butyl-[3-(1,4-dioxa-spiro[4.5]dec-2-yl)-3-(3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane

There total 13 articles about tert-butyl-[3-(1,4-dioxa-spiro[4.5]dec-2-yl)-3-(3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane 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: 97.0%

{3-[3-(tert-butyl-diphenyl-silanyloxy)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)-propyl]-oxiranyl}-methanol (935253-04-6) → tert-butyl-[3-(1,4-dioxa-spiro[4.5]dec-2-yl)-3-(3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane (935252-92-9)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1021/ol0700862

Reference yield:

3-allyl-butane-1,2,4-triol (935252-96-3) → tert-butyl-[3-(1,4-dioxa-spiro[4.5]dec-2-yl)-3-(3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane (935252-92-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 75 percent / p-TsOH / ethyl acetate / 12 h / 20 °C

2: 97 percent / pyridine / 0 - 20 °C

3: ozone / methanol; CH₂Cl₂ / -78 °C

4: 10.3 g / NaBH₄ / methanol; CH₂Cl₂ / -78 - -20 °C

5: 91 percent / imidazole / dimethylformamide / 4 h / 20 °C

6: 95 percent / K₂CO₃ / methanol / 72 h / 20 °C

7: 95 percent / [bis(acetoxy)iodo]benzene; TEMPO / CH₂Cl₂ / 1.5 h / 20 °C

8: 94 percent / CH₂Cl₂ / 12 h / 20 °C

9: 86 percent / i-Bu₂AlH / toluene; CH₂Cl₂ / 2 h / -78 °C

10: 80 percent / L-(+)-diisopropyl tatrtrate; Ti(OPr-i)4; t-BuO₂H / 4 Amgstroem molecular sieves / CH₂Cl₂ / 12 h / -20 °C

11: 97 percent / I₂; Ph₃P; imidazole / tetrahydrofuran; acetonitrile / 0.5 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; L-(+)-diisopropyl tartrate; [bis(acetoxy)iodo]benzene; iodine; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; triphenylphosphine; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 10: Sharpless asymmetric epoxidation;

DOI:10.1021/ol0700862

Reference yield:

2-(1,4-dioxa-spiro[4.5]dec-2-yl)-pent-4-en-1-ol (935252-97-4) → tert-butyl-[3-(1,4-dioxa-spiro[4.5]dec-2-yl)-3-(3-iodomethyl-oxiranyl)-propoxy]-diphenyl-silane (935252-92-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 97 percent / pyridine / 0 - 20 °C

2: ozone / methanol; CH₂Cl₂ / -78 °C

3: 10.3 g / NaBH₄ / methanol; CH₂Cl₂ / -78 - -20 °C

4: 91 percent / imidazole / dimethylformamide / 4 h / 20 °C

5: 95 percent / K₂CO₃ / methanol / 72 h / 20 °C

6: 95 percent / [bis(acetoxy)iodo]benzene; TEMPO / CH₂Cl₂ / 1.5 h / 20 °C

7: 94 percent / CH₂Cl₂ / 12 h / 20 °C

8: 86 percent / i-Bu₂AlH / toluene; CH₂Cl₂ / 2 h / -78 °C

9: 80 percent / L-(+)-diisopropyl tatrtrate; Ti(OPr-i)4; t-BuO₂H / 4 Amgstroem molecular sieves / CH₂Cl₂ / 12 h / -20 °C

10: 97 percent / I₂; Ph₃P; imidazole / tetrahydrofuran; acetonitrile / 0.5 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; L-(+)-diisopropyl tartrate; [bis(acetoxy)iodo]benzene; iodine; diisobutylaluminium hydride; potassium carbonate; ozone; triphenylphosphine; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 9: Sharpless asymmetric epoxidation;

DOI:10.1021/ol0700862

upstream raw materials:

{3-[3-(tert-butyl-diphenyl-silanyloxy)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)-propyl]-oxiranyl}-methanol

3-allyl-butane-1,2,4-triol

2-(1,4-dioxa-spiro[4.5]dec-2-yl)-pent-4-en-1-ol

benzoic acid 2-(1,4-dioxa-spiro[4.5]dec-2-yl)-pent-4-enyl ester

Downstream raw materials:

(1S,4S,5R,6R,8R)-4-<(tert-butyldiphenylsiloxy)methyl>-6-(hydroxymethyl)-8-isopropyl-8-methoxy-1-methyl-3,7-dioxabicyclo<3.3.0>octan-2-one

2,2-Dimethyl-propionic acid (1R,3R,3aS,6S,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-isopropyl-3-methoxy-3a-methyl-4-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

6-(tert-butyl-diphenyl-silanyloxy)-4-(1,4-dioxa-spiro[4.5]dec-2-yl)-hex-1-en-3-ol

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