(1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane

Base Information

Chemical Name:(1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane
CAS No.:321882-84-2
Molecular Formula:C₂₆H₃₅BO₃Si
Molecular Weight:434.459
Hs Code.:

Synonyms:(1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane

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Chemical Property of (1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane

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Technology Process of (1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane

There total 5 articles about (1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane 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:

: 321882-81-9
(1'R,2'R,4R,5R)-2-{2-[(E)-2-hydroxymethylethenyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

: 321882-84-2
(1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: ZnI₂ / CH₂Cl₂ / 0.08 h / 0 °C

1.3: Et₂Zn / CH₂Cl₂ / 12 h / 20 °C

2.1: 98 percent / imidazole / CH₂Cl₂ / 5 h / 0 °C

3.1: LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

4.1: 376 mg / pentane / 12 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; diethylzinc; (R,R)-1,2-bis(tosylamino)cyclohexane; In tetrahydrofuran; hexane; dichloromethane; pentane;
DOI:10.1021/jo0056601

Reference yield:

: 321882-80-8
(1'R,2'R,4R,5R)-2-{2'-[(E)-2-methoxycarbonylethenyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

: 321882-84-2
(1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

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

2.2: ZnI₂ / CH₂Cl₂ / 0.08 h / 0 °C

2.3: Et₂Zn / CH₂Cl₂ / 12 h / 20 °C

3.1: 98 percent / imidazole / CH₂Cl₂ / 5 h / 0 °C

4.1: LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

5.1: 376 mg / pentane / 12 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; diethylzinc; diisobutylaluminium hydride; (R,R)-1,2-bis(tosylamino)cyclohexane; In tetrahydrofuran; hexane; dichloromethane; pentane;
DOI:10.1021/jo0056601

Reference yield:

: 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

: 321882-84-2
(1'R,2'R,1''S,2''R)-2-{2-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]cyclopropyl}-1,3,2-dioxaborinane

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / imidazole / CH₂Cl₂ / 5 h / 0 °C

2: LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

3: 376 mg / pentane / 12 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1021/jo0056601