(1'R,2'R,4R,5R)-2-(2'-iodocyclopropyl)-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: (1'R,2'R,4R,5R)-2-(2'-iodocyclopropyl)-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane
• CAS No.: 771563-10-1
• Molecular Formula: C₃₃H₃₂BIO₄
• Molecular Weight: 630.33
• Mol file: 771563-10-1.mol

Synonyms:(1'R,2'R,4R,5R)-2-(2'-iodocyclopropyl)-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

Chemical Property of (1'R,2'R,4R,5R)-2-(2'-iodocyclopropyl)-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,2'R,4R,5R)-2-(2'-iodocyclopropyl)-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane

There total 2 articles about (1'R,2'R,4R,5R)-2-(2'-iodocyclopropyl)-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:

(1R,2R)-2-[(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolan-2-yl]-cyclopropanecarboxylic acid (771563-09-8) → (1'R,2'R,4R,5R)-2-(2'-iodocyclopropyl)-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane (771563-10-1) + (1'R,2'S,4R,5R)-2-(2'-iodocyclopropyl)-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane (771563-11-2)

Guidance literature:

(1R,2R)-2-[(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolan-2-yl]-cyclopropanecarboxylic acid; With dmap; [Me₂N-(1-oxy-pyridin-2-ylsulfanyl)-methylene]-NMe₂⁺ PF₆^-; triethylamine; In tetrahydrofuran; acetonitrile; at 20 ℃; for 1h;

With iodoform; at 80 ℃; for 24h; Further stages.;

DOI:10.1002/adsc.200404055

Reference yield:

(4R,5R,1'R,2'R)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane (321882-78-4) → (1'R,2'R,4R,5R)-2-(2'-iodocyclopropyl)-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane (771563-10-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / NaIO₄ / RuCl₃*3H₂O / CCl₄; H₂O; acetonitrile / 2 h / 40 °C

2.1: [Me₂N-(1-oxy-pyridin-2-ylsulfanyl)-methylene]-NMe₂⁺ PF₆^-; DMAP; Et₃N / acetonitrile; tetrahydrofuran / 1 h / 20 °C

2.2: iodoform / various solvent(s) / 24 h / 80 °C

With dmap; sodium periodate; [Me₂N-(1-oxy-pyridin-2-ylsulfanyl)-methylene]-NMe₂⁺ PF₆^-; triethylamine; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;

DOI:10.1002/adsc.200404055

Reference yield: 87.0%

phenylboronic acid (98-80-6) + (1'R,2'R,4R,5R)-2-(2'-iodocyclopropyl)-4,5-bis(methoxydiphenylmethyl)-1,3,2-dioxaborolane (771563-10-1) → (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((1R,2R)-2-phenyl-cyclopropyl)-[1,3,2]dioxaborolane

Guidance literature:

With potassium tert-butylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; tert-butyl alcohol; at 80 ℃; for 15h;

DOI:10.1002/adsc.200404055

upstream raw materials:

(1R,2R)-2-[(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolan-2-yl]-cyclopropanecarboxylic acid

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

Downstream raw materials:

(1'R,2'R,4R,5R)-4,5-bis(methoxydiphenylmethyl)-2-[2'-(2''-phenylcyclopropyl)cyclopropyl]-1,3,2-dioxaborolane

(1'R,2'R,4R,5R)-4,5-bis(methoxydiphenylmethyl)-2-(2'-phenylcyclopropyl)-1,3,2-dioxaborolane