(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-((1S,2S)-2-iodo-cyclopropyl)-4-methyl-pentan-1-ol

Base Information

• Chemical Name: (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-((1S,2S)-2-iodo-cyclopropyl)-4-methyl-pentan-1-ol
• CAS No.: 869338-44-3
• Molecular Formula: C₃₁H₄₉IO₃Si₂
• Molecular Weight: 652.804

Synonyms:(2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-((1S,2S)-2-iodo-cyclopropyl)-4-methyl-pentan-1-ol

Chemical Property of (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-((1S,2S)-2-iodo-cyclopropyl)-4-methyl-pentan-1-ol

Chemical Property:

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Technology Process of (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-((1S,2S)-2-iodo-cyclopropyl)-4-methyl-pentan-1-ol

There total 11 articles about (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-((1S,2S)-2-iodo-cyclopropyl)-4-methyl-pentan-1-ol 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: 70.0%

2-[1-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-4-iodo-but-3-en-1-ol (869338-43-2) + Chloroiodomethane (593-71-5) → (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-((1S,2S)-2-iodo-cyclopropyl)-4-methyl-pentan-1-ol (869338-44-3)

Guidance literature:

With diethylzinc; In 1,2-dichloro-ethane; at 20 ℃; for 3h;

DOI:10.1021/ol051691c

Reference yield:

(E)-(R)-5-(4-Methoxy-benzyloxy)-4-methyl-pent-2-enoic acid methyl ester (869338-51-2) → (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-((1S,2S)-2-iodo-cyclopropyl)-4-methyl-pentan-1-ol (869338-44-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / DIBAL / CH₂Cl₂; toluene / 2 h / -78 °C

2: 90 percent / 3 Angstroem molecular sieves; diethyl (+)-tartrate; t-BuOOH / Ti(O-iPr)4 / CH₂Cl₂; decane / 20 h / -30 °C

3: 67 percent / CuI

4: 95 percent / OsO₄; NaIO₄

5: 99 percent / DDQ / CH₂Cl₂ / 2 h / 0 °C

6: imidazole / dimethylformamide / 20 h / 20 °C

7: 0.91 g / aq. HCl / ethanol / 0.5 h / 20 °C

8: 70 percent / Et₂Zn / 1,2-dichloro-ethane / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; diethyl (2R,3R)-tartrate; 3 A molecular sieve; diethylzinc; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; In decane; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 6: Wittig reaction;

DOI:10.1021/ol051691c

Reference yield:

(2E,4R)-5-(4-methoxybenzyloxy)-4-methyl-2-penten-1-ol (200341-72-6) → (2R,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-((1S,2S)-2-iodo-cyclopropyl)-4-methyl-pentan-1-ol (869338-44-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / 3 Angstroem molecular sieves; diethyl (+)-tartrate; t-BuOOH / Ti(O-iPr)4 / CH₂Cl₂; decane / 20 h / -30 °C

2: 67 percent / CuI

3: 95 percent / OsO₄; NaIO₄

4: 99 percent / DDQ / CH₂Cl₂ / 2 h / 0 °C

5: imidazole / dimethylformamide / 20 h / 20 °C

6: 0.91 g / aq. HCl / ethanol / 0.5 h / 20 °C

7: 70 percent / Et₂Zn / 1,2-dichloro-ethane / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; diethyl (2R,3R)-tartrate; 3 A molecular sieve; diethylzinc; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; In decane; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 5: Wittig reaction;

DOI:10.1021/ol051691c

upstream raw materials:

2-[1-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propyl]-4-iodo-but-3-en-1-ol

Chloroiodomethane

(E)-(R)-5-(4-Methoxy-benzyloxy)-4-methyl-pent-2-enoic acid methyl ester

{(2S,3S)-3-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-oxiranyl}-methanol

Downstream raw materials:

1-[(Z)-(1S,2S)-1-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-methyl-hexa-3,5-dienyloxymethyl]-4-methoxy-benzene

(2S,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptan-1-ol

(2S,4S,5S)-4-((1R,2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{(1R,2R)-2-[(1S,2R,3S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxymethoxy-1,3-dimethyl-butyl]-cyclopropyl}-1,3-dimethyl-butyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

(2S,3R,4S)-4-{(1R,2R)-2-[(Z)-(2S,3R,4R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-deca-7,9-dienyl]-cyclopropyl}-3-methoxymethoxy-2-methyl-pentan-1-ol

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