(2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde

Base Information

• Chemical Name: (2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde
• CAS No.: 216769-50-5
• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.359
• Mol file: 216769-50-5.mol

Synonyms:(2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde

Chemical Property of (2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde

There total 10 articles about (2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde 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: 93.0%

(4R,5S,2'R,6'R)-2,2-dimethyl-5-(6'-hydroxymethylpyran-2'-yl)-4-phenyl-[1,3]dioxolane (216769-45-8) → (2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde (216769-50-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1039/b602805e

Reference yield:

(R,R)-2-(6'-tert-butyldiphenylsilanyloxymethylpyranyloxy)-1-phenylethanone (216769-05-0) → (2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde (216769-50-5)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂ / -78 - -30 °C

2: 1.13 g / TMSOTf / CH₂Cl₂ / 0.17 h / -30 °C

3: 100 percent / NaBH₄ / methanol / 0.02 h / 0 °C

4: 99 percent / (+/-)-camphorsulfonic acid / acetone / 0.5 h

5: 99 percent / TBAF / tetrahydrofuran / 2 h

6: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With sodium tetrahydroborate; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1039/b602805e

Reference yield:

(R)-1-(tert-butyldiphenylsilanyloxy)-hept-6-en-2-ol (216769-35-6) → (2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde (216769-50-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium bicarbonate; O₃ / CH₂Cl₂ / 0.5 h / -78 °C

1.2: 100 percent / PPh₃ / CH₂Cl₂ / 16 h / 20 °C

2.1: 81 percent / KHMDS / toluene; tetrahydrofuran / 2 h / -78 - 0 °C

3.1: 97 percent / tetrahydrofuran; diethyl ether / 0.5 h / -30 °C

4.1: Et₃N / CH₂Cl₂ / -78 - -30 °C

5.1: 1.13 g / TMSOTf / CH₂Cl₂ / 0.17 h / -30 °C

6.1: 100 percent / NaBH₄ / methanol / 0.02 h / 0 °C

7.1: 99 percent / (+/-)-camphorsulfonic acid / acetone / 0.5 h

8.1: 99 percent / TBAF / tetrahydrofuran / 2 h

9.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

With sodium tetrahydroborate; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene;

DOI:10.1039/b602805e

upstream raw materials:

(4R,5S,2'R,6'R)-2,2-dimethyl-5-(6'-hydroxymethylpyran-2'-yl)-4-phenyl-[1,3]dioxolane

(R)-1-(tert-butyldiphenylsilanyloxy)-hept-6-en-2-ol

(R)-6-(tert-butyldiphenylsilanyloxymethyl)-tetrahydropyran-2-ol

(R,R)-2-(6'-tert-butyldiphenylsilanyloxymethylpyranyloxy)-1-phenylethanone

Downstream raw materials:

(2R,6R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-carboxylic acid

(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one

(6R,4'S,5'R) 6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-pyranyl acetate

(R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-ol