(4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

Base Information

Chemical Name:(4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane
CAS No.:321882-83-1
Molecular Formula:C₅₃H₅₇BO₅Si
Molecular Weight:812.929
Hs Code.:

Synonyms:(4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

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Chemical Property of (4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

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Technology Process of (4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

There total 5 articles about (4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane 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: 98.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 321882-82-0
(4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-hydroxymethylcyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

: 321882-83-1
(4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 ℃; for 5h;
DOI:10.1021/jo0056601

Reference yield:

: 321882-78-4
(4R,5R,1'R,2'R)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane

: 321882-83-1
(4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

Guidance literature:: Multi-step reaction with 5 steps

1.1: TPAP; NMO; 4 Angstroem MS / CH₂Cl₂ / 12 h / 20 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 19.56 g / tetrahydrofuran / 12 h / 20 °C

3.1: 97 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

4.1: (R,R)-N,N'-ditosylcyclohexane-1,2-diamine; Et₂Zn / CH₂Cl₂; hexane / 0.17 h / 0 °C

4.2: ZnI₂ / CH₂Cl₂ / 0.08 h / 0 °C

4.3: Et₂Zn / CH₂Cl₂ / 12 h / 20 °C

5.1: 98 percent / imidazole / CH₂Cl₂ / 5 h / 0 °C

With 1H-imidazole; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; diethylzinc; sodium hydride; diisobutylaluminium hydride; (R,R)-1,2-bis(tosylamino)cyclohexane; In tetrahydrofuran; hexane; dichloromethane; 2.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0056601

Reference yield:

: 321882-79-5
(1R,2R)-2-[(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolan-2-yl]-cyclopropanecarbaldehyde

: 321882-83-1
(4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: 19.56 g / tetrahydrofuran / 12 h / 20 °C

2.1: 97 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

3.1: (R,R)-N,N'-ditosylcyclohexane-1,2-diamine; Et₂Zn / CH₂Cl₂; hexane / 0.17 h / 0 °C

3.2: ZnI₂ / CH₂Cl₂ / 0.08 h / 0 °C

3.3: Et₂Zn / CH₂Cl₂ / 12 h / 20 °C

4.1: 98 percent / imidazole / CH₂Cl₂ / 5 h / 0 °C

With 1H-imidazole; diethylzinc; sodium hydride; diisobutylaluminium hydride; (R,R)-1,2-bis(tosylamino)cyclohexane; In tetrahydrofuran; hexane; dichloromethane; 1.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo0056601