(4S,5S)-4,5-bis{[3-(diphenylphosphanyl)biphenyl-2-yloxy]methyl}-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4S,5S)-4,5-bis{[3-(diphenylphosphanyl)biphenyl-2-yloxy]methyl}-2,2-dimethyl-1,3-dioxolane
• CAS No.: 1643966-17-9
• Molecular Formula: C₅₅H₄₈O₄P₂
• Molecular Weight: 834.931
• Mol file: 1643966-17-9.mol

Synonyms:(4S,5S)-4,5-bis{[3-(diphenylphosphanyl)biphenyl-2-yloxy]methyl}-2,2-dimethyl-1,3-dioxolane

Chemical Property of (4S,5S)-4,5-bis{[3-(diphenylphosphanyl)biphenyl-2-yloxy]methyl}-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4,5-bis{[3-(diphenylphosphanyl)biphenyl-2-yloxy]methyl}-2,2-dimethyl-1,3-dioxolane

There total 3 articles about (4S,5S)-4,5-bis{[3-(diphenylphosphanyl)biphenyl-2-yloxy]methyl}-2,2-dimethyl-1,3-dioxolane 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: 96.0%

C55H54B2O4P2 → (4S,5S)-4,5-bis{[3-(diphenylphosphanyl)biphenyl-2-yloxy]methyl}-2,2-dimethyl-1,3-dioxolane (1643966-17-9)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In toluene; at 50 ℃; for 5h; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.201402326

Reference yield:

(-)-dimethy-2,3-O-isopropylidene-L-tartrate (37031-29-1) → (4S,5S)-4,5-bis{[3-(diphenylphosphanyl)biphenyl-2-yloxy]methyl}-2,2-dimethyl-1,3-dioxolane (1643966-17-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere; Reflux; Schlenk technique

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique

2.2: Inert atmosphere; Schlenk technique

3.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 5 h / 50 °C / Inert atmosphere; Schlenk technique

With 1,4-diaza-bicyclo[2.2.2]octane; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; 2.1: |Mitsunobu Displacement / 2.2: |Mitsunobu Displacement;

DOI:10.1002/ejoc.201402326

Reference yield:

2-boranatodiphenylphosphanyl-6-phenylphenol (1158430-35-3) + 2,3-O-isopropylidene-L-threitol (50622-09-8) → (4S,5S)-4,5-bis{[3-(diphenylphosphanyl)biphenyl-2-yloxy]methyl}-2,2-dimethyl-1,3-dioxolane (1643966-17-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique

1.2: Inert atmosphere; Schlenk technique

2.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 5 h / 50 °C / Inert atmosphere; Schlenk technique

With 1,4-diaza-bicyclo[2.2.2]octane; di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; toluene; 1.1: |Mitsunobu Displacement / 1.2: |Mitsunobu Displacement;

DOI:10.1002/ejoc.201402326

upstream raw materials:

2-boranatodiphenylphosphanyl-6-phenylphenol

2,3-O-isopropylidene-L-threitol

(-)-dimethy-2,3-O-isopropylidene-L-tartrate