(R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol

Base Information

• Chemical Name: (R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol
• CAS No.: 895532-69-1
• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.391
• Mol file: 895532-69-1.mol

Synonyms:(R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol

Chemical Property of (R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol

There total 8 articles about (R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol 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%

ethyl (R)-3-benzyloxy-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropanoate → (R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol (895532-69-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃;

DOI:10.1055/s-0031-1290489

Reference yield:

3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropionic acid methyl ester → (R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol (895532-69-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / N-methylmorpholine N-oxide monohydrate; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / acetonitrile; CH₂Cl₂ / 0.5 h

2: zinc borohydride / diethyl ether / 1 h / -100 - -40 °C

3: 92 percent / sodium hydride / dimethylformamide / 0 - 20 °C

4: 100 percent / lithium aluminum hydride / tetrahydrofuran / 8 h / 0 - 20 °C

With lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 4 A molecular sieve; zinc borohydride; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo070861r

Reference yield:

(R)-methyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3-oxopropanoate (895532-67-9) → (R)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol (895532-69-1)

Guidance literature:

Multi-step reaction with 3 steps

1: zinc borohydride / diethyl ether / 1 h / -100 - -40 °C

2: 92 percent / sodium hydride / dimethylformamide / 0 - 20 °C

3: 100 percent / lithium aluminum hydride / tetrahydrofuran / 8 h / 0 - 20 °C

With lithium aluminium tetrahydride; zinc borohydride; sodium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo070861r

upstream raw materials:

(R)-methyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3-oxopropanoate

(R)-3-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-2,2-dimethylpropionic acid methyl ester

benzyl bromide

(R)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2,2-dimethylpropanoate

Downstream raw materials:

(3R,4R)-3-(benzyloxy)-4,5-dihydroxy-2,2-dimethylpentyl acetate

(R)-3-(benzyloxy)-2,2-dimethyl-4-oxobutyl acetate

(2R)-4-acetoxy-2-(benzyloxy)-3,3-dimethylbutanoic acid

methyl 3-[(R)-4-acetoxy-2-(benzyloxy)-3,3-dimethylbutanoylamino]propanoate

Refernces

• 1、 Paquette, Leo A.,Parker, Gregory D.,Tei, Takahiro,Dong, Shuzhi. "Pestalotiopsin A. Enantioselective construction of potential building blocks derived from antipodal cyclobutanol intermediates". . p. 7124 - 7134. Retrieved 2008/02/11.