alpha-D-erythro-Pentofuranose, 3-azido-4-C-[(benzoyloxy)methyl]-3-deoxy-1,2-O-(1-methylethylidene)-, 5-benzoate

Base Information

• Chemical Name: alpha-D-erythro-Pentofuranose, 3-azido-4-C-[(benzoyloxy)methyl]-3-deoxy-1,2-O-(1-methylethylidene)-, 5-benzoate
• CAS No.: 153914-98-8
• Molecular Formula: C₂₃H₂₃N₃O₇
• Molecular Weight: 453.452
• DSSTox Substance ID: DTXSID201109859
• Nikkaji Number: J1.164.634D
• Mol file: 153914-98-8.mol

Synonyms:SCHEMBL15677986;DTXSID201109859;153914-98-8;alpha-D-erythro-Pentofuranose, 3-azido-4-C-[(benzoyloxy)methyl]-3-deoxy-1,2-O-(1-methylethylidene)-, 5-benzoate

Chemical Property of alpha-D-erythro-Pentofuranose, 3-azido-4-C-[(benzoyloxy)methyl]-3-deoxy-1,2-O-(1-methylethylidene)-, 5-benzoate

Chemical Property:

• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 453.15360008
• Heavy Atom Count: 33
• Complexity: 736

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)(COC(=O)C3=CC=CC=C3)COC(=O)C4=CC=CC=C4)N=[N+]=[N-])C
• Isomeric SMILES: CC1(O[C@@H]2[C@@H](C(O[C@@H]2O1)(COC(=O)C3=CC=CC=C3)COC(=O)C4=CC=CC=C4)N=[N+]=[N-])C

Technology Process of alpha-D-erythro-Pentofuranose, 3-azido-4-C-[(benzoyloxy)methyl]-3-deoxy-1,2-O-(1-methylethylidene)-, 5-benzoate

There total 9 articles about alpha-D-erythro-Pentofuranose, 3-azido-4-C-[(benzoyloxy)methyl]-3-deoxy-1,2-O-(1-methylethylidene)-, 5-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: 86.0%

→ 3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (153914-98-8) + 3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (247025-10-1)

Guidance literature:

Reference yield:

C24H23F3O10S (153915-02-7) → 3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (153914-98-8)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 1h; Yield given;

Reference yield:

5-O-benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose (153914-97-7) → 3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (153914-98-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine, EtOH / CH₂Cl₂ / 0.17 h / Ambient temperature

2: NaN₃ / dimethylformamide / 2 h / 100 °C

With pyridine; sodium azide; ethanol; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/15257779408013221

upstream raw materials:

C₂₄H₂₃F₃O₁₀S

benzoyl chloride

1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

5-O-benzoyl-4-benzoyloxymethyl-1,2-O-isopropylidene-α-D-xylofuranose

Downstream raw materials:

1-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)uracil

9-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)uracil

9-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)-N⁶-benzoyladenine

1-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)-N⁴-acetylcytosine