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

Base Information

Chemical Name:3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-ethoxymethylene-1,2-isopropylidene-β-D-ribo-pentofuranose
CAS No.:851345-97-6
Molecular Formula:C₃₄H₄₄O₆Si
Molecular Weight:576.805
Hs Code.:

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

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Chemical Property of 3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-ethoxymethylene-1,2-isopropylidene-β-D-ribo-pentofuranose

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Technology Process of 3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-ethoxymethylene-1,2-isopropylidene-β-D-ribo-pentofuranose

There total 1 articles about 3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-ethoxymethylene-1,2-isopropylidene-β-D-ribo-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: 63.0%

: 75-03-6
ethyl iodide

: 212970-72-4
{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

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

Guidance literature:: {3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

ethyl iodide; In N,N-dimethyl-formamide; at -20 - 0 ℃; for 4h;
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

: 1-(5'-O-(4,4'-dimethoxytrityl)-4'-C-ethoxymethyl-β-D-ribo-pentofuranosyl)thymine

Guidance literature:: Multi-step reaction with 9 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

4: 94 percent / NaOMe / methanol / 1 h / 20 °C

5: 85 percent / DMAP / acetonitrile / 1 h / 20 °C

6: 69 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

7: TBAF / tetrahydrofuran / 24 h / 20 °C

8: 19 mg / H₂ / Pd(OH)2/C / ethanol / 6 h / 60 °C

9: 25 percent / DMAP; pyridine / 4 h / 50 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium methylate; acetic acid; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; toluene; acetonitrile; 3: Vorbrueggen glycosylation;
DOI:10.1002/chem.200401114