5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose

Base Information

Chemical Name:5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose
CAS No.:446862-76-6
Molecular Formula:C₃₅H₄₂O₁₁SSi
Molecular Weight:698.863
Hs Code.:

Synonyms:5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose

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Chemical Property of 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose

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Technology Process of 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose

There total 5 articles about 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose 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:

: 108-24-7
acetic anhydride

: 212970-73-5
3-O-benzyl-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyl)oxymethyl-α-D-erythro-pentofuranose

: 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-α-D-erythro-pentofuranose

: 446862-76-6
5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose

Guidance literature:: 3-O-benzyl-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyl)oxymethyl-α-D-erythro-pentofuranose; With sulfuric acid; In acetic acid; at 20 ℃; for 2h;

With hydrogen; palladium on activated charcoal; In chloroform; ethyl acetate; at 20 ℃; for 16h;

acetic anhydride; In pyridine; at 20 ℃; for 49h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4020(02)00227-2

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 446862-76-6
5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: 97 percent / 4,4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

2.1: conc. H₂SO₄ / acetic acid / 2 h / 20 °C

2.2: H₂ / 10 percent Pd/C / ethyl acetate; CHCl₃ / 16 h / 20 °C

2.3: pyridine / 49 h / 20 °C

With dmap; sulfuric acid; In dichloromethane; acetic acid;
DOI:10.1016/S0040-4020(02)00227-2

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 446862-76-6
5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: 67 percent / CH₂Cl₂ / 11 h / 20 °C

2.1: 97 percent / 4,4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

3.1: conc. H₂SO₄ / acetic acid / 2 h / 20 °C

3.2: H₂ / 10 percent Pd/C / ethyl acetate; CHCl₃ / 16 h / 20 °C

3.3: pyridine / 49 h / 20 °C

With dmap; sulfuric acid; In dichloromethane; acetic acid;
DOI:10.1016/S0040-4020(02)00227-2