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

Base Information

• Chemical Name: (4R,5R,1'R,2'R)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane
• CAS No.: 321882-78-4
• Molecular Formula: C₃₄H₃₅BO₅
• Molecular Weight: 534.46
• Mol file: 321882-78-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (4R,5R,1'R,2'R)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (4R,5R)-2-[(E)-2-{hydroxymethyl}ethenyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane (251956-33-9) → (4R,5R,1'R,2'R)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane (321882-78-4) + (4R,5R,1'S,2'S)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane

Guidance literature:

With palladium diacetate; In diethyl ether; at 0 ℃;

DOI:10.1021/jo9910278

Reference yield:

diiodomethane (75-11-6) + (4R,5R)-2-[(E)-2-{hydroxymethyl}ethenyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane (251956-33-9) → (4R,5R,1'R,2'R)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane (321882-78-4) + (4R,5R,1'S,2'S)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane

Guidance literature:

(4R,5R)-2-[(E)-2-{hydroxymethyl}ethenyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane; In dichloromethane; at 0 ℃; for 0.166667h;

diiodomethane; With zinc(II) iodide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/jo9910278

Reference yield:

(4R,5R)-4,5-bis(methoxymethyl)-2-(p-methoxyphenyl)-α,α,α',α'-tetraphenyl-1,3-dioxolane (130888-43-6) → (4R,5R,1'R,2'R)-2-[2-(hydroxymethyl)cyclopropyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane (321882-78-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 2,3-dichloro-4,5-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 2 h / 20 °C

1.2: LiAlH₄ / diethyl ether / 2 h / 20 °C

2.1: BH₃*SMe₂ / CH₂Cl₂ / 4 h / Heating

3.1: 12 h / 120 °C

4.1: 98 percent / HF / acetonitrile / 0.33 h / 20 °C

5.1: Pd(OAc)2 / diethyl ether / 0 °C

With palladium diacetate; dimethylsulfide borane complex; hydrogen fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; acetonitrile; 1.1: Ring cleavage / 1.2: Reduction / 2.1: Cycloaddition / 3.1: Addition / 4.1: desilylation / 5.1: Cycloaddition;

DOI:10.1021/jo9910278

upstream raw materials:

diazomethane

(4R,5R)-2-[(E)-2-{hydroxymethyl}ethenyl]-4,5-bis[methoxy(diphenyl)methyl]-1,3,2-dioxaborolane

diiodomethane

(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol

Downstream raw materials:

(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

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

(1S,2R,1'R,2'R)-2'-[(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolan-2-yl]-bicyclopropyl-2-carboxylic acid

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