((2R,3S,5S)-3-(Benzoyloxy)-5-cyanotetrahydrofuran-2-yl)methyl benzoate

Base Information

• Chemical Name: ((2R,3S,5S)-3-(Benzoyloxy)-5-cyanotetrahydrofuran-2-yl)methyl benzoate
• CAS No.: 127676-66-8
• Molecular Formula: C₂₀H₁₇NO₅
• Molecular Weight: 0
• DSSTox Substance ID: DTXSID401183324
• Mol file: 127676-66-8.mol

Synonyms:127676-66-8;((2R,3S,5S)-3-(Benzoyloxy)-5-cyanotetrahydrofuran-2-yl)methyl benzoate;[(2R,3S,5S)-3-benzoyloxy-5-cyanooxolan-2-yl]methyl benzoate;D-arabino-Hexononitrile, 2,5-anhydro-3-deoxy-, 4,6-dibenzoate (9CI);DTXSID401183324;A889160;(2R,3S,5S)-2-[(benzoyloxy)methyl]-5-cyanooxolan-3-yl benzoate;D-arabino-Hexononitrile, 2,5-anhydro-3-deoxy-, 4,6-dibenzoate;((2R,3S,5S)-3-(Benzoyloxy)-5-cyanotetrahydrofuran-2-yl)methylbenzoate

Chemical Property of ((2R,3S,5S)-3-(Benzoyloxy)-5-cyanotetrahydrofuran-2-yl)methyl benzoate

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 351.11067264
• Heavy Atom Count: 26
• Complexity: 542

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(C1OC(=O)C2=CC=CC=C2)COC(=O)C3=CC=CC=C3)C#N
• Isomeric SMILES: C1[C@H](O[C@@H]([C@H]1OC(=O)C2=CC=CC=C2)COC(=O)C3=CC=CC=C3)C#N

Technology Process of ((2R,3S,5S)-3-(Benzoyloxy)-5-cyanotetrahydrofuran-2-yl)methyl benzoate

There total 3 articles about ((2R,3S,5S)-3-(Benzoyloxy)-5-cyanotetrahydrofuran-2-yl)methyl benzoate 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:

C20H15NO5 (127676-65-7) → C20H17NO5 (127691-81-0) + C20H17NO5 (127676-66-8)

Guidance literature:

With hydrogen; Pd-BaSO₄; In ethanol; at 25 ℃;

DOI:10.1039/c39900000084

Reference yield:

2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl cyanide (38642-50-1) → C20H17NO5 (127676-66-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂

2: H₂ / Pd/BaSO₄ / ethanol / 25 °C

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; Pd-BaSO₄; In ethanol; dichloromethane;

DOI:10.1039/c39900000084

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → C20H17NO5 (127676-66-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / pyridine / 4 h / Ambient temperature

2: BF₃*OEt₂ / CH₂Cl₂ / 5 h / Ambient temperature

With pyridine; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1246/cl.1992.1673

upstream raw materials:

C₂₀H₁₅NO₅

D-2-deoxyribose

2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl cyanide

Downstream raw materials:

methyl 6-(3',5'-di-O-benzoyl-2'-deoxy-α-D-ribofuranosyl)nicotinate

4-(3',5'-di-O-benzoyl-2'-deoxy-α-D-ribofuranosyl)pyrimidine

2-pyridyl 3,5-di-O-benzoyl-2-deoxy-1-thio-α,β-D-ribofuranoside

2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-arabino-hexonic acid