N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam

Base Information

• Chemical Name: N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam
• CAS No.: 1338787-20-4
• Molecular Formula: C₁₆H₂₁NO₆S
• Molecular Weight: 355.412
• Mol file: 1338787-20-4.mol

Synonyms:N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam

Chemical Property of N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam

There total 4 articles about N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam 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: 97.0%

methanesulfonyl chloride (124-63-0) + N-benzyl-4-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactam (192317-22-9) → N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam (1338787-20-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/j.bmc.2011.07.043

Reference yield:

1-amino-1,4-anhydro-N-benzyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol (153172-30-6) → N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam (1338787-20-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium periodate; ruthenium(IV) oxide hydrate / ethyl acetate / 20 h / 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

3: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C

With sodium periodate; ruthenium(IV) oxide hydrate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1016/j.bmc.2011.07.043

Reference yield:

N-benzyl-5-O-tert-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactam (1338787-49-7) → N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam (1338787-20-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

2: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2011.07.043

upstream raw materials:

N-benzyl-5-O-tert-butyldimethylsilyl-4-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactam

methanesulfonyl chloride

N-benzyl-4-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactam

N-benzyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Downstream raw materials:

S-(N-benzyl-4,5-dideoxy-D-ribono-1,4-lactam-5-yl)-1-homocysteine

S-(N-benzyl-4,5-dideoxy-2,3-O-isopropylidene-D-ribono-1,4-lactam-5-yl)-N-(tert-butoxycarbonyl)-1-homocysteine tert-butyl ester