[[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di(R)-ethylidene]bis-[diphenylphosphine]

Base Information

• Chemical Name: [[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di(R)-ethylidene]bis-[diphenylphosphine]
• CAS No.: 258873-45-9
• Molecular Formula: C₃₃H₃₆O₂P₂
• Molecular Weight: 526.595
• Mol file: 258873-45-9.mol

Synonyms:[[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di(R)-ethylidene]bis-[diphenylphosphine]

Chemical Property of [[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di(R)-ethylidene]bis-[diphenylphosphine]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di(R)-ethylidene]bis-[diphenylphosphine]

There total 8 articles about [[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di(R)-ethylidene]bis-[diphenylphosphine] 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: 67.0%

diphenylphosphane (829-85-6) + 3,4-O-isopropylidene-(3S,4S)-dihydroxy-(2S,5S)-hexanediol bis(methanesulfonate) (259136-24-8) → [[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di(R)-ethylidene]bis-[diphenylphosphine] (258873-45-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo0004613

Reference yield: 49.0%

chloro-diphenylphosphine (1079-66-9,74391-44-9) + 3,4-O-isopropylidene-(3S,4S)-dihydroxy-(2S,5S)-hexanediol bis(methanesulfonate) (259136-24-8) → [[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di(R)-ethylidene]bis-[diphenylphosphine] (258873-45-9)

Guidance literature:

With lithium; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1021/jo991762j

Reference yield:

1,6-di-O-benzoyl-3,4-di-O-isopropylidene-D-mannitol (51432-64-5) → [[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di(R)-ethylidene]bis-[diphenylphosphine] (258873-45-9)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine; DMAP / 4 h / 0 °C

2: K₂CO₃ / methanol / 20 °C

3: 83 percent / LiEt₃BH / tetrahydrofuran / 0 °C

4: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

5: 67 percent / n-BuLi / tetrahydrofuran / 0 - 20 °C

With pyridine; dmap; n-butyllithium; lithium triethylborohydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1: Tosylation / 2: Cyclization / 3: Reduction / 4: Condensation / 5: Substitution;

DOI:10.1021/jo0004613

upstream raw materials:

chloro-diphenylphosphine

3,4-O-isopropylidene-(3S,4S)-dihydroxy-(2S,5S)-hexanediol bis(methanesulfonate)

diphenylphosphane

1,6-di-O-benzoyl-3,4-di-O-isopropylidene-D-mannitol