(-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL

Base Information

• Chemical Name: (-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL
• CAS No.: 137365-09-4
• Molecular Formula: C47H38 O4
• Molecular Weight: 666.816
• Mol file: 137365-09-4.mol

Synonyms:1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-a,a,a',a'-tetra-2-naphthalenyl-, (4R,5R)- (9CI); 1,3-Dioxolane-4,5-dimethanol,2,2-dimethyl-a,a,a',a'-tetra-2-naphthalenyl-, (4R-trans)-; (4R,5R)-2,2-Dimethyl-a,a,a',a'-tetra-2-naphthalenyl-1,3-dioxolane-4,5-dimethanol

Chemical Property of (-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL

Chemical Property:

• Melting Point: 213-216 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 58.92000
• Density: 1.269g/cm³
• LogP: 9.99150
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

(4R,5R)-2,2-Dimethyl-α,α,α'',α''-tetra-2-naphthalenyl-1,3-dioxolane-4,5-dimethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (4R,5R)-2,2-Dimethyl-α,α,α'',α''-tetra-2-naphthalenyl-1,3-dioxolane-4,5-dimethanol, is a privileged ligand analogue of TADDOLs. It can be broadly used in asymmetric synthesis. It is also shown that the titanium TADDOLate catalysts have broad application towards carbonyl addition and cycloaddition.

Technology Process of (-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL

There total 5 articles about (-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRA(2-NAPHTHYL)-L-THREITOL 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: 91.8%

2-bromonaphthalene (580-13-2) + diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8) → [(4R,5R)-2,2-dimethyl-1,3-dioxolan-4,5-diyl]bis(dinaphthalen-2-ylmethanol) (137365-09-4,137365-16-3)

Guidance literature:

2-bromonaphthalene; With isopropylmagnesium bromide; In tetrahydrofuran; at 0 - 6 ℃; for 0.5h; Inert atmosphere;

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate; In tetrahydrofuran; at 68 ℃; for 4h;

Reference yield: 82.0%

(-)-dimethy-2,3-O-isopropylidene-L-tartrate (37031-29-1) + 2-bromonaphthalene (580-13-2) → [(4R,5R)-2,2-dimethyl-1,3-dioxolan-4,5-diyl]bis(dinaphthalen-2-ylmethanol) (137365-09-4,137365-16-3)

Guidance literature:

2-bromonaphthalene; With iodine; magnesium; In tetrahydrofuran; for 1.75h; Inert atmosphere; Reflux;

(-)-dimethy-2,3-O-isopropylidene-L-tartrate; In tetrahydrofuran; at 20 ℃; for 1.83h; Reflux;

DOI:10.15227/orgsyn.076.0012

Reference yield:

C14H16N2*C47H38O4 → (R,R)-1,2-diphenylethylenediamine (35132-20-8) + [(4R,5R)-2,2-dimethyl-1,3-dioxolan-4,5-diyl]bis(dinaphthalen-2-ylmethanol) (137365-09-4,137365-16-3)

Guidance literature:

In chloroform-d1; Equilibrium constant;

DOI:10.1021/ja907826z

upstream raw materials:

2-bromonaphthalene

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

C₁₄H₁₆N₂*C₄₇H₃₈O₄

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

Downstream raw materials:

6-(2-diphenylphosphanyl-6-isopropylphenoxy)-2,2-dimethyl-4,4,8,8-tetranaphthalen-2-yltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine

6-(2-tert-butyl-6-diphenylphosphanylphenoxy)-2,2-dimethyl-4,4,8,8-tetranaphthalen-2-yltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine

6-(2,4-di-tert-butyl-6-diphenylphosphanylphenoxy)-2,2-dimethyl-4,4,8,8-tetranaphthalen-2-yltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine

6-(3-diphenylphosphanylbiphenyl-2-yloxy)-2,2-dimethyl-4,4,8,8-tetranaphthalen-2-yltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine