(2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol

Base Information

• Chemical Name: (2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol
• CAS No.: 202526-16-7
• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.391
• Mol file: 202526-16-7.mol

Synonyms:(2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol

Chemical Property of (2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol

There total 5 articles about (2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-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: 94.0%

[(2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butoxy]-tert-butyl-dimethyl-silane (202526-33-8) → (2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol (202526-16-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/jo971863m

Reference yield:

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (32233-44-6) → (2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol (202526-16-7)

Guidance literature:

Multi-step reaction with 5 steps

1: CH₂Cl₂ / -78 - 0 °C

2: 60 percent / LAH / tetrahydrofuran / 0 °C

3: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 25 °C

4: 85 percent / NaH / dimethylformamide / 25 °C

5: 94 percent / TBAF / tetrahydrofuran / 25 °C

With dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo971863m

Reference yield:

(2R,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butane-1,3-diol (202526-15-6) → (2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol (202526-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 25 °C

2: 85 percent / NaH / dimethylformamide / 25 °C

3: 94 percent / TBAF / tetrahydrofuran / 25 °C

With dmap; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo971863m

upstream raw materials:

[(2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butoxy]-tert-butyl-dimethyl-silane

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

(2R,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butane-1,3-diol

(2S,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-butan-2-ol

Downstream raw materials:

(2S,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butyraldehyde

[(3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

(3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-one

((2S,3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester