alpha-D-Ribofuranose, 3-deoxy-3-(hydroxyamino)-1,2-O-(1-methylethylidene)-, 5-benzoate

Base Information

• Chemical Name: alpha-D-Ribofuranose, 3-deoxy-3-(hydroxyamino)-1,2-O-(1-methylethylidene)-, 5-benzoate
• CAS No.: 83905-12-8
• Molecular Formula: C₁₅H₁₉NO₆
• Molecular Weight: 309.319
• DSSTox Substance ID: DTXSID801131551
• Mol file: 83905-12-8.mol

Synonyms:DTXSID801131551;alpha-D-Ribofuranose, 3-deoxy-3-(hydroxyamino)-1,2-O-(1-methylethylidene)-, 5-benzoate;83905-12-8

Chemical Property of alpha-D-Ribofuranose, 3-deoxy-3-(hydroxyamino)-1,2-O-(1-methylethylidene)-, 5-benzoate

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 309.12123733
• Heavy Atom Count: 22
• Complexity: 409

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)COC(=O)C3=CC=CC=C3)NO)C
• Isomeric SMILES: CC1(O[C@@H]2[C@@H]([C@H](O[C@@H]2O1)COC(=O)C3=CC=CC=C3)NO)C

Technology Process of alpha-D-Ribofuranose, 3-deoxy-3-(hydroxyamino)-1,2-O-(1-methylethylidene)-, 5-benzoate

There total 2 articles about alpha-D-Ribofuranose, 3-deoxy-3-(hydroxyamino)-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: 89.0%

(E/Z)-5-O-Benzoyl-3-deoxy-3-hydroxyimino-1,2-O-isopropylidene-α-D-erythro-pentofuranose (29781-91-7) → O-benzoyl-5-desoxy-3-hydroxyamino-3-O-isopropylidene-1,2-α-D-ribofuranose (83905-12-8)

Guidance literature:

With sodium cyanoborohydride; In methanol; for 2h;

DOI:10.1002/hlca.19860690521

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) → O-benzoyl-5-desoxy-3-hydroxyamino-3-O-isopropylidene-1,2-α-D-ribofuranose (83905-12-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 91.4 percent / NH₂OH*HCl / pyridine; ethanol / 1 h / Heating

2: 89 percent / NaBH₃CN / methanol / 2 h

With hydroxylamine hydrochloride; sodium cyanoborohydride; In pyridine; methanol; ethanol;

DOI:10.1002/hlca.19860690521

Reference yield: 91.0%

acetic anhydride (108-24-7) + O-benzoyl-5-desoxy-3-hydroxyamino-3-O-isopropylidene-1,2-α-D-ribofuranose (83905-12-8) → 3-acetoxyamino-5-O-benzoyl-3-deoxy-1,2-isopropylidene-α-D-ribofuranose

Guidance literature:

In acetone; for 0.0833333h;

DOI:10.1002/prac.19943360318

upstream raw materials:

(E/Z)-5-O-Benzoyl-3-deoxy-3-hydroxyimino-1,2-O-isopropylidene-α-D-erythro-pentofuranose

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose

Downstream raw materials:

Benzoic acid (3aR,5S,6R,6aR)-2,2-dimethyl-6-nitroso-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester