2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol

Base Information

• Chemical Name: 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol
• CAS No.: 111550-04-0
• Molecular Formula: C₅₈H₆₈O₁₀Si
• Molecular Weight: 953.257
• Mol file: 111550-04-0.mol

Synonyms:

Chemical Property of 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol

There total 17 articles about 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-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: 68.0%

2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol (111550-03-9,121700-67-2) + tert-butylchlorodiphenylsilane (58479-61-1) → 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol (111550-04-0,121700-68-3)

Guidance literature:

In pyridine; for 5h; Ambient temperature;

DOI:10.1002/recl.19871060905

Reference yield:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol (111550-04-0,121700-68-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 40 percent / silver oxide / dimethylformamide / 48 h / in dark

2: 80 percent / sodium borohydride / tetrahydrofuran / 55 °C / 2.) methanol 45 min and 1h

3: acetic acid; H₂O / 4 h / 50 °C

4: pyridine / Ambient temperature

5: 86 percent / 1.) sodium hydride / dimethylformamide / 1.) 0 deg C 30 min; 2.) 0 deg C 30 min; 3.) room temperature overnight

6: 90 percent / acetic acid; H₂O / 1.5 h / 80 °C

7: 1.) molecular sieves 4 Angstroem; 2.) trimethylsilyl trifluoromethanesulfonate / 1.) 1,2-dichloroethane, 90 min, room temperature; 2.) 1,2-dichloroethane, room temperature 2 h and 3 h

8: 88 percent / sodium methoxide / dioxane; methanol / 5 h / Ambient temperature

9: 67 percent / pyridine / 1.) 0 deg C, 15 min; 2.) room temperature, 60 min

10: 85 percent / N,N-diisopropylethylamine / acetonitrile / 3 h / 50 °C

11: (1,5-cyclooctadiene)-bis(methyldiphenylphosphine)iridium hexafluorophosphate activated by hydrogen / tetrahydrofuran / 4 h / four times degassed and placed under helium

12: 63 percent / tetra n-butylammonium fluoride / dioxane / 0.5 h / Ambient temperature

13: 68 percent / pyridine / 5 h / Ambient temperature

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; N-ethyl-N,N-diisopropylamine; silver(l) oxide; (1,5-cyclooctadiene)-bis(methyldiphenylphosphine)iridium hexafluorophosphate activated by hydrogen; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/recl.19871060905

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol (111550-04-0,121700-68-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) molecular sieves 4 Angstroem; 2.) trimethylsilyl trifluoromethanesulfonate / 1.) 1,2-dichloroethane, 90 min, room temperature; 2.) 1,2-dichloroethane, room temperature 2 h and 3 h

2: 88 percent / sodium methoxide / dioxane; methanol / 5 h / Ambient temperature

3: 67 percent / pyridine / 1.) 0 deg C, 15 min; 2.) room temperature, 60 min

4: 85 percent / N,N-diisopropylethylamine / acetonitrile / 3 h / 50 °C

5: (1,5-cyclooctadiene)-bis(methyldiphenylphosphine)iridium hexafluorophosphate activated by hydrogen / tetrahydrofuran / 4 h / four times degassed and placed under helium

6: 63 percent / tetra n-butylammonium fluoride / dioxane / 0.5 h / Ambient temperature

7: 68 percent / pyridine / 5 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; N-ethyl-N,N-diisopropylamine; (1,5-cyclooctadiene)-bis(methyldiphenylphosphine)iridium hexafluorophosphate activated by hydrogen; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; acetonitrile;

DOI:10.1002/recl.19871060905

upstream raw materials:

2,3,4-tri-O-benzyl-1-O-<2'-O-(benzyloxymethyl)-β-D-ribofuranosyl>-5-O-(trans-1-propenyl)-D-ribitol

tert-butylchlorodiphenylsilane

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

2,3-O-isopropylidene-D-ribonic-γ-lactone

Downstream raw materials:

C₁₁₅H₁₄₂ClO₂₃PSi₃