(3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanone

Base Information

• Chemical Name: (3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanone
• CAS No.: 263155-20-0
• Molecular Formula: C₂₀H₃₂O₄Si
• Molecular Weight: 364.557

Synonyms:(3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanone

Chemical Property of (3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanone

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanone

There total 3 articles about (3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanone 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: 88.0%

(3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanol (228267-27-4) → (3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanone (263155-20-0)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1016/S0968-0896(00)00125-5

Reference yield:

((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-acetaldehyde (72496-37-8) → (3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanone (263155-20-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / n-BuLi / tetrahydrofuran / -70 °C

2: 88 percent / tetrapropylammonium perruthenate; 4-methylmorpholine / CH₂Cl₂

With 4-methyl-morpholine; n-butyllithium; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.48.310

Reference yield:

4-(tert-butyldimethylsiloxymethyl)bromobenzene (87736-74-1) → (3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanone (263155-20-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / n-BuLi / tetrahydrofuran / -70 °C

2: 88 percent / tetrapropylammonium perruthenate; 4-methylmorpholine / CH₂Cl₂

With 4-methyl-morpholine; n-butyllithium; tetrapropylammonium perruthennate; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.48.310

upstream raw materials:

(3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanol

((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-acetaldehyde

4-(tert-butyldimethylsiloxymethyl)bromobenzene

Downstream raw materials:

(1S,3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanol

(2R,4R)-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonyl-4-mesyloxypyrrolidine

(2R,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine

Methanesulfonic acid (1R,3R)-3-allyloxycarbonylamino-3-[4-(allyloxycarbonylamino-methyl)-phenyl]-1-methanesulfonyloxymethyl-propyl ester

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