(2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-3,4-dihydroxy-5-[(p-toluenesulfonyl)oxy]pentane

Base Information

• Chemical Name: (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-3,4-dihydroxy-5-[(p-toluenesulfonyl)oxy]pentane
• CAS No.: 270571-09-0
• Molecular Formula: C₂₉H₃₅NO₆SSi
• Molecular Weight: 553.751
• Mol file: 270571-09-0.mol

Synonyms:(2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-3,4-dihydroxy-5-[(p-toluenesulfonyl)oxy]pentane

Chemical Property of (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-3,4-dihydroxy-5-[(p-toluenesulfonyl)oxy]pentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-3,4-dihydroxy-5-[(p-toluenesulfonyl)oxy]pentane

There total 5 articles about (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-3,4-dihydroxy-5-[(p-toluenesulfonyl)oxy]pentane 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'S)-3-(1',4'-dioxa-spiro[4.5]dec-2'-yl)-prop-2-en-1-ol (124988-77-8) → (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-3,4-dihydroxy-5-[(p-toluenesulfonyl)oxy]pentane (270571-09-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / tert-butylhydroperoxide; titanium tetraisopropoxide; diethyl L-(+)-tartrate / CH₂Cl₂; decane / 16 h / -15 °C

2.1: tetrabutylammonium iodide; titanium tetraisopropoxide / dimethylsulfoxide / 60 h / 20 °C

2.2: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

3.1: HOAc (80percent) / 40 h / 20 °C

4.1: 1.6 g / pyridine / 4 h / 20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; tetra-(n-butyl)ammonium iodide; In decane; dichloromethane; dimethyl sulfoxide; 1.1: Sharpless asymmetric epoxidation / 2.1: Ring cleavage / 2.2: silylation / 3.1: Ring cleavage / 4.1: Tosylation;

DOI:10.1021/jo9917700

Reference yield:

(E)-(S)-3-(1,4-Dioxa-spiro[4.5]dec-2-yl)-acrylic acid methyl ester → (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-3,4-dihydroxy-5-[(p-toluenesulfonyl)oxy]pentane (270571-09-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / DIBAL / toluene; CH₂Cl₂ / 2 h / 20 °C

2.1: 90 percent / tert-butylhydroperoxide; titanium tetraisopropoxide; diethyl L-(+)-tartrate / CH₂Cl₂; decane / 16 h / -15 °C

3.1: tetrabutylammonium iodide; titanium tetraisopropoxide / dimethylsulfoxide / 60 h / 20 °C

3.2: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

4.1: HOAc (80percent) / 40 h / 20 °C

5.1: 1.6 g / pyridine / 4 h / 20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; In decane; dichloromethane; dimethyl sulfoxide; toluene; 1.1: Reduction / 2.1: Sharpless asymmetric epoxidation / 3.1: Ring cleavage / 3.2: silylation / 4.1: Ring cleavage / 5.1: Tosylation;

DOI:10.1021/jo9917700

Reference yield:

(2S,3R,4R)-2,3-epoxy-4,5-(cyclohexylidenedioxy)pentan-1-ol (270571-07-8) → (2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-3,4-dihydroxy-5-[(p-toluenesulfonyl)oxy]pentane (270571-09-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrabutylammonium iodide; titanium tetraisopropoxide / dimethylsulfoxide / 60 h / 20 °C

1.2: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: HOAc (80percent) / 40 h / 20 °C

3.1: 1.6 g / pyridine / 4 h / 20 °C

With pyridine; titanium(IV) isopropylate; tetra-(n-butyl)ammonium iodide; In dimethyl sulfoxide; 1.1: Ring cleavage / 1.2: silylation / 2.1: Ring cleavage / 3.1: Tosylation;

DOI:10.1021/jo9917700

upstream raw materials:

p-toluenesulfonyl chloride

(2'S)-3-(1',4'-dioxa-spiro[4.5]dec-2'-yl)-prop-2-en-1-ol

(2S,3R,4R)-2,3-epoxy-4,5-(cyclohexylidenedioxy)pentan-1-ol

(2R,3R,4R)-1-[(tert-butyldiphenylsilyl)oxy]-2-cyano-4,5-(cyclohexylidenedioxy)-3-hydroxypentane

Downstream raw materials:

tert-butyl (3R,4R,5R)-5-[(tert-butyldiphenylsilyl)oxy]-3,4-dihydroxypiperidine-1-carboxylate

isofagomine

(3R,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-piperidine-3,4-diol