5-Deoxy-1-O,2-O-isopropylidene-α-D-erythro-3-pentulofuranose

Base Information

• Chemical Name: 5-Deoxy-1-O,2-O-isopropylidene-α-D-erythro-3-pentulofuranose
• CAS No.: 32453-67-1
• Molecular Formula: C8H12O4
• Molecular Weight: 172.181
• Hs Code.: 2932999099
• Mol file: 32453-67-1.mol

Synonyms:5-Deoxy-1-O,2-O-isopropylidene-α-D-erythro-3-pentulofuranose

Chemical Property of 5-Deoxy-1-O,2-O-isopropylidene-α-D-erythro-3-pentulofuranose

Chemical Property:

• PSA: 44.76000
• LogP: 0.45180

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Deoxy-1-O,2-O-isopropylidene-α-D-erythro-3-pentulofuranose

There total 6 articles about 5-Deoxy-1-O,2-O-isopropylidene-α-D-erythro-3-pentulofuranose 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: 99.0%

1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose (4152-79-8,33156-02-4,37105-87-6,37105-91-2,37105-93-4,53597-97-0,97059-40-0) → 5-deoxy-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (32453-67-1)

Guidance literature:

With dipyridinium dichromate; acetic anhydride; In dichloromethane; for 1.5h; Reflux;

DOI:10.1002/cctc.201402933

Reference yield:

5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-D-xylofuranose (50600-39-0) → 5-deoxy-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (32453-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / Et₃N, H₂ / 5percent Pd/C / methanol / 16 h / Ambient temperature

2: Ac₂O/DMSO / 20 h / Ambient temperature

With hydrogen; acetic anhydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol;

DOI:10.1002/hlca.19820650525

Reference yield:

1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose (6893-65-8,20513-95-5,20513-96-6,34981-06-1,40429-51-4,110349-61-6) → 5-deoxy-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (32453-67-1)

Guidance literature:

Multi-step reaction with 3 steps

1: NaI / hexamethylphosphoric acid triamide / 12 h / 100 °C

2: Na(CN)BH₃ / hexamethylphosphoric acid triamide / 15 h / 100 °C

3: 90 percent / H₂O, KIO₄, K₂CO₃, RuO₂ / CH₂Cl₂ / 3 h

With ruthenium(IV) oxide; potassium metaperiodate; water; sodium cyanoborohydride; potassium carbonate; sodium iodide; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1139/v84-442

upstream raw materials:

1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose

5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-D-xylofuranose

1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose

1,2-O-isopropylidene-α-D-xylose

Downstream raw materials:

doxifluridine

1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil

5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose

(E)-(4S,5R)-4-Allyloxy-5-formyloxy-hex-2-enoic acid 2-(toluene-4-sulfonyl)-ethyl ester