(4R,5R)-2-((S)-1-chloro-3-phenylpropyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: (4R,5R)-2-((S)-1-chloro-3-phenylpropyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane
• CAS No.: 1402010-06-3
• Molecular Formula: C₂₃H₃₄BClO₂
• Molecular Weight: 388.786

Synonyms:(4R,5R)-2-((S)-1-chloro-3-phenylpropyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane

Chemical Property of (4R,5R)-2-((S)-1-chloro-3-phenylpropyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane

Chemical Property:

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Technology Process of (4R,5R)-2-((S)-1-chloro-3-phenylpropyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane

There total 2 articles about (4R,5R)-2-((S)-1-chloro-3-phenylpropyl)-4,5-dicyclohexyl-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:

dichloromethane (75-09-2) + (4R,5R)-4,5-dicyclohexyl-2-phenethyl-1,3,2-dioxaborolane (1402010-05-2) → (4R,5R)-2-((S)-1-chloro-3-phenylpropyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane (1402010-06-3)

Guidance literature:

dichloromethane; With n-butyllithium; In tetrahydrofuran; at -78 - -70 ℃; for 0.0833333h;

(4R,5R)-4,5-dicyclohexyl-2-phenethyl-1,3,2-dioxaborolane; With zinc(II) chloride; In tetrahydrofuran; at -78 - 20 ℃; for 36h; stereospecific reaction;

DOI:10.1021/ja307861n

Reference yield:

(1R,2R)-1,2-dicyclohexyl-1,2-ethanediol (120850-92-2) → (4R,5R)-2-((S)-1-chloro-3-phenylpropyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane (1402010-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diethyl ether / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 0.08 h / -78 - -70 °C

2.2: 36 h / -78 - 20 °C

With n-butyllithium; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja307861n

Reference yield: 92.0%

potassium hydrogen difluoride + (4R,5R)-2-((S)-1-chloro-3-phenylpropyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane (1402010-06-3) → potassium (R)-1-(benzyloxy)-3-phenylpropyltrifluoroboranuide

Guidance literature:

In methanol; water; acetonitrile; at 20 ℃; stereospecific reaction;

DOI:10.1021/ja307861n

upstream raw materials:

dichloromethane

(4R,5R)-4,5-dicyclohexyl-2-phenethyl-1,3,2-dioxaborolane

(1R,2R)-1,2-dicyclohexyl-1,2-ethanediol

Downstream raw materials:

C₂₂H₂₁FO

C₂₆H₂₅NO

C₂₂H₂₃NO₂

(4R,5R)-2-((R)-1-(benzyloxy)-3-phenylpropyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane

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