β-4,5-dibenzoyl-2-cyano-D-deoxyribrate

Base Information

• Chemical Name: β-4,5-dibenzoyl-2-cyano-D-deoxyribrate
• CAS No.: 170983-98-9
• Molecular Formula: C20H21NO3
• Molecular Weight: 323.392
• Mol file: 170983-98-9.mol

Synonyms:3,5-di-O-benzyl-2-deoxy-β-D-ribofuranosyl cyanide;SS-4,5-DIBENZOYL-2-CYANO-D-DEOXYRIBRATE;

Chemical Property of β-4,5-dibenzoyl-2-cyano-D-deoxyribrate

Chemical Property:

• PSA: 51.48000
• LogP: 3.46968

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of β-4,5-dibenzoyl-2-cyano-D-deoxyribrate

There total 14 articles about β-4,5-dibenzoyl-2-cyano-D-deoxyribrate 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: 67.0%

methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside (132487-16-2) + trimethylsilyl cyanide (7677-24-9) → 1β-cyano-3,5-di-O-benzyl-1,2-dideoxy-D-ribofuranose (170983-98-9) + 1α-cyano-3,5-di-O-benzyl-1,2-dideoxy-D-ribofuranose (226232-74-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.3987/COM-14-S(K)41

Reference yield:

3,5-di-O-benzyl-2-deoxy-D-ribofuranose (6160-50-5) → 1β-cyano-3,5-di-O-benzyl-1,2-dideoxy-D-ribofuranose (170983-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 0.5 h / 20 °C

2: BF₃*Et₂O / acetonitrile / 0.5 h / -40 °C

With pyridine; boron trifluoride diethyl etherate; In acetonitrile; 1: Acetylation / 2: Substitution;

DOI:10.1515/znb-1999-0420

Reference yield:

trimethylsilyl cyanide (7677-24-9) + D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) + benzyl bromide (100-39-0) → 1β-cyano-3,5-di-O-benzyl-1,2-dideoxy-D-ribofuranose (170983-98-9) + 1α-cyano-3,5-di-O-benzyl-1,2-dideoxy-D-ribofuranose (226232-74-2)

Guidance literature:

D-2-deoxyribose; With acetyl chloride; silver carbonate; In methanol; at 20 ℃; for 0.116667h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at -30 - 20 ℃; for 24h;

trimethylsilyl cyanide; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(99)02078-X

upstream raw materials:

1-O-acetyl-3,5-di-O-benzyl-2-deoxy-D-erythro-pentofuranose

trimethylsilyl cyanide

D-2-deoxyribose

benzyl bromide

Downstream raw materials:

3,5-Di-O-benzyl-2-desoxy-β-D-ribofuranose-1-imidocarbonsaeuremethylester

5-(3',5'-Di-O-benzyl-2'-desoxy-β-D-ribofuranosyl)-3,6-bis(trifluoromethyl)-1,2,4-triazin