4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-altro-oct-2-ynitol

Base Information

• Chemical Name: 4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-altro-oct-2-ynitol
• CAS No.: 1449683-05-9
• Molecular Formula: C₂₇H₃₄O₄Si
• Molecular Weight: 450.65
• Mol file: 1449683-05-9.mol

Synonyms:4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-altro-oct-2-ynitol

Chemical Property of 4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-altro-oct-2-ynitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-altro-oct-2-ynitol

There total 1 articles about 4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-altro-oct-2-ynitol 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: 56.0%

1-propynyltributylstannane (64099-82-7) + 1-O-acetyl-5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranose (82921-64-0) → 4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-altro-oct-2-ynitol (1449683-05-9) + 4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-allo-oct-2-ynitol (1449683-06-0)

Guidance literature:

1-propynyltributylstannane; 1-O-acetyl-5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranose; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 0.75h; Inert atmosphere;

DOI:10.1002/chem.201301230

Reference yield: 69.0%

4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-altro-oct-2-ynitol (1449683-05-9) → 4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1-deoxy-5,6-O-isopropylidene-D-altro-octo-2,3-diulose (1449682-29-4) + 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3)

Guidance literature:

With sodium periodate; ruthenium(IV) oxide hydrate; In tetrachloromethane; [⁽²⁾H₆]acetone; water; at 20 ℃; for 0.833333h; Darkness;

DOI:10.1002/chem.201301230

Reference yield:

4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-D-altro-oct-2-ynitol (1449683-05-9) → 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium periodate; ruthenium(IV) oxide hydrate / water; tetrachloromethane; [⁽²⁾H₆]acetone / 0.83 h / 20 °C / Darkness

2: benzene-d6 / 2 h / 30 °C / Photolysis

3: silica gel; oxygen / ethyl acetate; hexane

With sodium periodate; ruthenium(IV) oxide hydrate; oxygen; silica gel; In tetrachloromethane; [⁽²⁾H₆]acetone; hexane; benzene-d6; water; ethyl acetate;

DOI:10.1002/chem.201301230

upstream raw materials:

1-propynyltributylstannane

1-O-acetyl-5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranose

Downstream raw materials:

4,7-anhydro-8-O-(tert-butyldiphenylsilyl)-1-deoxy-5,6-O-isopropylidene-D-altro-octo-2,3-diulose

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

Refernces