1-(2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

Base Information

Chemical Name:1-(2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine
CAS No.:851345-99-8
Molecular Formula:C₃₈H₄₆N₂O₈Si
Molecular Weight:686.877
Hs Code.:

Synonyms:1-(2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

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Chemical Property of 1-(2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

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Technology Process of 1-(2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

There total 4 articles about 1-(2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine 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 acid (2R,3R,4S,5R)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-ethoxymethyl-tetrahydro-furan-3-yl ester

: 65-71-4,28806-14-6,691841-57-3
thymin

: 851345-99-8
1-(2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

Guidance literature:: With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 1h; Heating;
DOI:10.1002/chem.200401114

Reference yield:

: (2S,3R,4S,5R)-4-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-ethoxymethyl-tetrahydro-furan-2,3-diol

: 851345-99-8
1-(2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 2 steps

1: 150.8 mg / DMAP; pyridine / 18 h / 20 °C

2: 91 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 1 h / Heating

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; 2: Vorbrueggen glycosylation;
DOI:10.1002/chem.200401114

Reference yield:

: 851345-97-6
3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-ethoxymethylene-1,2-isopropylidene-β-D-ribo-pentofuranose

: 851345-99-8
1-(2'-O-acetyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-ethoxymethylene-β-D-ribo-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 3 steps

1: aq. AcOH; CF₃COOH / 4 h / 20 °C

2: 150.8 mg / DMAP; pyridine / 18 h / 20 °C

3: 91 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 1 h / Heating

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; acetic acid; trifluoroacetic acid; In acetonitrile; 3: Vorbrueggen glycosylation;
DOI:10.1002/chem.200401114