3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-ido-oct-1-ynitol

Base Information

• Chemical Name: 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-ido-oct-1-ynitol
• CAS No.: 443915-97-7
• Molecular Formula: C₃₂H₃₇N₃O₄Si
• Molecular Weight: 555.749
• Mol file: 443915-97-7.mol

Synonyms:3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-ido-oct-1-ynitol

Chemical Property of 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-ido-oct-1-ynitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-ido-oct-1-ynitol

There total 2 articles about 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-ido-oct-1-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: 43.0%

(trimethylsilylethynyl)tributyltin (81353-38-0) + 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate (443915-94-4) → 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose (55682-48-9) + 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-ido-oct-1-ynitol (443915-97-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jo020054m

Reference yield:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose → 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-ido-oct-1-ynitol (443915-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: 43 percent / 4 Angstroem molecular sieves; trimethylsilyl triflate / CH₂Cl₂ / 3 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane;

DOI:10.1021/jo020054m

Reference yield: 99.0%

3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-ido-oct-1-ynitol (443915-97-7) → 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol (443916-33-4)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo020054m

upstream raw materials:

(trimethylsilylethynyl)tributyltin

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate

Downstream raw materials:

3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol