(4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-hydroxymethylcyclopropyl]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-hydroxymethylcyclopropyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane
CAS No.:321882-82-0
Molecular Formula:C₃₇H₃₉BO₅
Molecular Weight:574.525
Hs Code.:

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

There total 4 articles about (4R,5R,1'R,2'R,1''S,2''R)-2-{2-[2-hydroxymethylcyclopropyl]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:

: 75-11-6
diiodomethane

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

: 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

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

Guidance literature:: (1'R,2'R,4R,5R)-2-{2-[(E)-2-hydroxymethylethenyl]cyclopropyl}-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane; With diethylzinc; (R,R)-1,2-bis(tosylamino)cyclohexane; In hexane; dichloromethane; at 0 ℃; for 0.166667h;

With zinc(II) iodide; In dichloromethane; at 0 ℃; for 0.0833333h;

diiodomethane; With diethylzinc; In dichloromethane; at 20 ℃; for 12h; Further stages.;
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

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

Guidance literature:: Multi-step reaction with 4 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

With 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

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

Guidance literature:: Multi-step reaction with 3 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

With 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