(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((Z)-styryl)-[1,3,2]dioxaborolane

Base Information

• Chemical Name: (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((Z)-styryl)-[1,3,2]dioxaborolane
• CAS No.: 296241-78-6
• Molecular Formula: C₃₈H₃₅BO₄
• Molecular Weight: 566.504
• Mol file: 296241-78-6.mol

Synonyms:(4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((Z)-styryl)-[1,3,2]dioxaborolane

Chemical Property of (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((Z)-styryl)-[1,3,2]dioxaborolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((Z)-styryl)-[1,3,2]dioxaborolane

There total 3 articles about (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((Z)-styryl)-[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: 77.0%

(Z)-styryl iodide (57918-63-5) + (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol (130874-89-4) → (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((Z)-styryl)-[1,3,2]dioxaborolane (296241-78-6)

Guidance literature:

(Z)-styryl iodide; With tert.-butyl lithium; In diethyl ether; at -78 ℃; for 2h;

With Triisopropyl borate; In diethyl ether; at -78 - 20 ℃;

(2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol; In diethyl ether; at 20 ℃; for 18h; Further stages.;

DOI:10.1002/1099-0690(200007)2000:14<2557::aid-ejoc2557>3.0.co;2-i

Reference yield:

1-iodo-2-phenylethyne (932-88-7) → (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((Z)-styryl)-[1,3,2]dioxaborolane (296241-78-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dipotassium azodicarboxylate / methanol; pyridine / 0 °C

2.1: tBuLi / diethyl ether / 2 h / -78 °C

2.2: B(OiPr)3 / diethyl ether / -78 - 20 °C

2.3: 77 percent / diethyl ether / 18 h / 20 °C

With tert.-butyl lithium; potassium diazodicarboxylate; In pyridine; methanol; diethyl ether; 1.1: Reduction / 2.1: Metallation / 2.2: hydroboration / 2.3: Esterification;

DOI:10.1002/1099-0690(200007)2000:14<2557::aid-ejoc2557>3.0.co;2-i

Reference yield:

phenylacetylene (536-74-3) → (4R,5R)-4,5-Bis-(methoxy-diphenyl-methyl)-2-((Z)-styryl)-[1,3,2]dioxaborolane (296241-78-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / -78 - 20 °C

1.2: 80 percent / I₂ / tetrahydrofuran / -78 - 20 °C

2.1: dipotassium azodicarboxylate / methanol; pyridine / 0 °C

3.1: tBuLi / diethyl ether / 2 h / -78 °C

3.2: B(OiPr)3 / diethyl ether / -78 - 20 °C

3.3: 77 percent / diethyl ether / 18 h / 20 °C

With n-butyllithium; tert.-butyl lithium; potassium diazodicarboxylate; In tetrahydrofuran; pyridine; methanol; diethyl ether; 1.1: Metallation / 1.2: Iodination / 2.1: Reduction / 3.1: Metallation / 3.2: hydroboration / 3.3: Esterification;

DOI:10.1002/1099-0690(200007)2000:14<2557::aid-ejoc2557>3.0.co;2-i

upstream raw materials:

(Z)-styryl iodide

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

1-iodo-2-phenylethyne

phenylacetylene