5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose

Base Information

• Chemical Name: 5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose
• CAS No.: 872345-49-8
• Molecular Formula: C₃₆H₄₁N₃O₅Si
• Molecular Weight: 623.824
• Mol file: 872345-49-8.mol

Synonyms:5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose

Chemical Property of 5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose

There total 1 articles about 5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose 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:

5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose (872345-46-5) + tert-butylchlorodiphenylsilane (58479-61-1) → 5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose (872345-49-8) + 5-azido-3,4-di-O-benzyl-1,6-di-O-tert-butyldiphenylsilyl-5-deoxy-D-psicose (872345-48-7)

Guidance literature:

5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose; With trifluoroacetic acid; at 20 ℃; for 2h;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1016/j.tet.2005.09.043

Reference yield: 77.0%

5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose (872345-49-8) → (3S,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ2-pyrroline

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; for 7h; Heating;

DOI:10.1016/j.tet.2005.09.043

Reference yield: 62.0%

5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose (872345-49-8) → (2R,3S,4R,5R)-3,4-bis(benzyloxy)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine (872345-56-7)

Guidance literature:

With hydrogen; nickel; In methanol; for 20h; under 3102.89 Torr;

DOI:10.1016/j.tet.2005.09.043

upstream raw materials:

5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2R,3S,4R,5R)-3,4-bis(benzyloxy)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine

(2S,3S,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine