5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-D-ribitol

Base Information

• Chemical Name: 5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-D-ribitol
• CAS No.: 117326-02-0
• Molecular Formula: C₄₅H₆₀O₁₀Si
• Molecular Weight: 789.051

Synonyms:5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-D-ribitol

Chemical Property of 5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-D-ribitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-D-ribitol

There total 13 articles about 5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-D-ribitol 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:

sodium hydrogencarbonate (144-55-8) + 5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-5-O-(trimethylacetyl)-D-ribitol (117326-01-9) → 5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-D-ribitol (117326-02-0)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; dichloromethane;

Reference yield:

2,3,4-Tris-O-(phenylmethyl)-5-O-(trimethylacetyl)-D-ribose diethyldithioacetal (117325-95-8) → 5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-D-ribitol (117326-02-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) HgCl₂, CdCO₃, 2.) NaBH₃CN, further reducing agent and solvent / 1.) acetone-water, 2.) dimethoxyethane

2: 97 percent / silver perchlorate, 4-Angstroem molecular sieves / acetonitrile / -40 °C

3: 2.) pyridine

4: Bu₄NI, DMAP, diisopropylethylamine / tetrahydrofuran / 96 h / Ambient temperature

5: tetra-n-butylammonium fluoride

6: 96 percent / silver nitrate, DMAP / tetrahydrofuran

7: LiEt₃BH / tetrahydrofuran / 3 h / 25 °C

With dmap; cadmium(II) carbonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver perchlorate; tetra-(n-butyl)ammonium iodide; lithium triethylborohydride; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; mercury dichloride; dmap; silver nitrate; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4039(00)80342-1

Reference yield:

(2R,3R,4R)-2,3,4-Trihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentanal (225797-51-3) → 5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-D-ribitol (117326-02-0)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium hydride / dimethylformamide

2: p-toluenesulfonic acid / methanol

3: 98 percent / pyridine / DMAP / CH₂Cl₂ / Ambient temperature

4: 1.) HgCl₂, CdCO₃, 2.) NaBH₃CN, further reducing agent and solvent / 1.) acetone-water, 2.) dimethoxyethane

5: 97 percent / silver perchlorate, 4-Angstroem molecular sieves / acetonitrile / -40 °C

6: 2.) pyridine

7: Bu₄NI, DMAP, diisopropylethylamine / tetrahydrofuran / 96 h / Ambient temperature

8: tetra-n-butylammonium fluoride

9: 96 percent / silver nitrate, DMAP / tetrahydrofuran

10: LiEt₃BH / tetrahydrofuran / 3 h / 25 °C

With pyridine; dmap; cadmium(II) carbonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; sodium cyanoborohydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; mercury dichloride; dmap; silver nitrate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(00)80342-1

upstream raw materials:

5-O-[(1,1-Dimethylethyl)dimethylsilyl]-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-5-O-(trimethylacetyl)-D-ribitol

Benzyloxymethyl chloride

(2R,3R,4R)-2,3,4-Trihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentanal

2,3,4-Tris-O-(phenylmethyl)-5-O-(trimethylacetyl)-D-ribitol

Downstream raw materials:

(2R,3R,4R,5R)-4-Benzyloxymethoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-{(2S,3R,4R)-2,3,4-tris-benzyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxy]-pentyloxy}-tetrahydro-furan-3-ol

5-O-[(1,1-Dimethylethyl)dimethylsilyl]-3-O-(1,4-dioxopentyl)-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-D-ribitol

5-O-[(1,1-Dimethylethyl)dimethylsilyl]-3-O-(1,4-dioxopentyl)-2-O-[(phenylmethoxy)methyl]-β-D-ribofuranosyl-2,3,4-tris-O-(phenylmethyl)-5-O-[(4-methoxyphenyl)-diphenylmethyl]-D-ribitol

5-O-[(1,1-Dimethylethyl)dimethylsilyl]-3-O-[[bis(1-methylethyl)amino]methoxyphosphino]-2-O-[(phenylmethoxy) methyl]-β-D-ribofuranosyl-5-O-[(4-methoxyphenyl)diphenylmethyl]-2,3,4-tris-O-(phenylmethyl)-D-ribitol

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