Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester
• CAS No.: 260269-28-1
• Molecular Formula: C₃₅H₄₂O₁₁SSi
• Molecular Weight: 698.863
• Mol file: 260269-28-1.mol

Synonyms:Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

Chemical Property of Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

There total 7 articles about Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester 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: 91.0%

acetic anhydride (108-24-7) + Acetic acid (3R,4S,5S)-2-acetoxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester → Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (260269-28-1)

Guidance literature:

In pyridine; at 20 ℃; for 20h;

DOI:10.1039/a907218g

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (260269-28-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

2: 86 percent / AcOH; H₂SO₄ / 0.5 h / 20 °C

3: H₂ / 10 percent Pd/C / ethyl acetate; CHCl₃ / 17 h / 20 °C

4: 91 percent / pyridine / 20 h / 20 °C

With dmap; sulfuric acid; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In pyridine; dichloromethane; chloroform; ethyl acetate; 1: Tosylation / 2: Acetylation / 3: Hydrogenolysis / 4: Acetylation;

DOI:10.1039/a907218g

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (260269-28-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 67 percent / Et₃N / CH₂Cl₂ / 14 h / 20 °C

2: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

3: 86 percent / AcOH; H₂SO₄ / 0.5 h / 20 °C

4: H₂ / 10 percent Pd/C / ethyl acetate; CHCl₃ / 17 h / 20 °C

5: 91 percent / pyridine / 20 h / 20 °C

With dmap; sulfuric acid; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In pyridine; dichloromethane; chloroform; ethyl acetate; 1: Etherification / 2: Tosylation / 3: Acetylation / 4: Hydrogenolysis / 5: Acetylation;

DOI:10.1039/a907218g

upstream raw materials:

acetic anhydride

p-toluenesulfonyl chloride

tert-butylchlorodiphenylsilane

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Downstream raw materials:

5'-O-tert-butyldiphenylsilyl-N²-isobutyryl-4'-C-(p-toluenesulfonyl)oxymethylguanosine

5'-O-tert-butyldiphenylsilyl-5-methyl-3'-O,4'-C-methyleneuridine

N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine

N⁶-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methyleneadenosine