(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-<2-(5-methylfuryl)>-1,2,3-propanetriol

Base Information

• Chemical Name: (2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-<2-(5-methylfuryl)>-1,2,3-propanetriol
• CAS No.: 107941-09-3
• Molecular Formula: C₂₇H₃₄O₄Si
• Molecular Weight: 450.65
• Mol file: 107941-09-3.mol

Synonyms:(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-<2-(5-methylfuryl)>-1,2,3-propanetriol

Chemical Property of (2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-<2-(5-methylfuryl)>-1,2,3-propanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-<2-(5-methylfuryl)>-1,2,3-propanetriol

There total 2 articles about (2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-<2-(5-methylfuryl)>-1,2,3-propanetriol 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:

2-methylfuran (534-22-5) → (2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-<2-(5-methylfuryl)>-1,2,3-propanetriol (107941-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) butyllithium 2.) ZnBr₂ / tetrahydrofuran; hexane / 1.) from -30 deg C to 10 deg C, 4 h 2.) 15 min 3.) -40 deg C, 4 h, then to 0 deg C, within 3 h

2: 91 percent / imidazole / dimethylformamide / 5 h / 80 °C

With 1H-imidazole; n-butyllithium; zinc dibromide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/ja00247a025

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-<2-(5-methylfuryl)>-1,2,3-propanetriol (107941-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) butyllithium 2.) ZnBr₂ / tetrahydrofuran; hexane / 1.) from -30 deg C to 10 deg C, 4 h 2.) 15 min 3.) -40 deg C, 4 h, then to 0 deg C, within 3 h

2: 91 percent / imidazole / dimethylformamide / 5 h / 80 °C

With 1H-imidazole; n-butyllithium; zinc dibromide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/ja00247a025

Reference yield: 82.0%

(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-<2-(5-methylfuryl)>-1,2,3-propanetriol (107941-09-3) → E-(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-octene-4,7-dione-1,2,3-triol (107941-13-9)

Guidance literature:

With pyridine; bromine; In water; acetonitrile; 1.) -20 deg C 2.) rt, 2 h;

DOI:10.1021/ja00247a025

upstream raw materials:

2-methylfuran

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

E-(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-octene-4,7-dione-1,2,3-triol

E-(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-octene-4,7-dione-1,2,3-triol, 7-dimethyl ketal

(E)-(1R,2S)-1-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5-dimethoxy-hex-3-en-2-ol

(E)-(2R,3S,4S)-4-O-acetyl-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-octen-7-one-1,2,3,4-tetraol