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

Base Information

• Chemical Name: 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
• CAS No.: 1338787-22-6
• Molecular Formula: C₂₈H₄₂N₂O₇S
• Molecular Weight: 550.717
• Mol file: 1338787-22-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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: 70.0%

N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam (1338787-20-4) + N-tert-butoxycarbonyl-L-homocysteine tert-butyl ester (630108-94-0) → 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 (1338787-22-6)

Guidance literature:

N-tert-butoxycarbonyl-L-homocysteine tert-butyl ester; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; N,N-dimethyl-formamide; at 0 ℃; for 0.25h; Inert atmosphere;

N-benzyl-4-deoxy-2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactam; In tetrahydrofuran; n-heptane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.07.043

Reference yield:

N,N′-di(tert-butoxycarbonyl)-L-homocystine di(tert-butyl)ester (601491-40-1) → 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 (1338787-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tris-(2-carboxyethyl)-phosphine hydrochloride / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere

2.2: 24 h / 0 - 20 °C / Inert atmosphere

With tris-(2-carboxyethyl)-phosphine hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; N,N-dimethyl-formamide;

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) → 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 (1338787-22-6)

Guidance literature:

Multi-step reaction with 4 steps

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

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

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

4.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere

4.2: 24 h / 0 - 20 °C / Inert atmosphere

With sodium periodate; ruthenium(IV) oxide hydrate; tetrabutyl ammonium fluoride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

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

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

N-tert-butoxycarbonyl-L-homocysteine tert-butyl ester

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