2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone

Base Information

• Chemical Name: 2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone
• CAS No.: 100776-48-5
• Molecular Formula: C₂₅H₄₃NO₆Si₂
• Molecular Weight: 509.791
• Mol file: 100776-48-5.mol

Synonyms:2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone

Chemical Property of 2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone

There total 4 articles about 2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone 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%

tert-butyldimethylsilyl chloride (18162-48-6) + (3S,4S,5R)-(4-hydroxy-5-hydroxymethyl-2-oxotetrahydrofuran-3-yl)carbamic acid benzyl ester (81366-43-0) → 2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone (100776-48-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 3h; Ambient temperature;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone (100776-48-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.6 g / NaHCO₃ / H₂O; diethyl ether / 1.) 5 h, below 10 deg C, 2.) RT_., 6 h

2: 86 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

With 1H-imidazole; sodium hydrogencarbonate; In diethyl ether; water; N,N-dimethyl-formamide;

Reference yield:

(2S,3S,4R)-3,4,5-trihydroxy-2-amino pentanoic acid (100741-07-9) → 2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone (100776-48-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.6 g / NaHCO₃ / H₂O; diethyl ether / 1.) 5 h, below 10 deg C, 2.) RT_., 6 h

2: 86 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

With 1H-imidazole; sodium hydrogencarbonate; In diethyl ether; water; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyldimethylsilyl chloride

(3S,4S,5R)-(4-hydroxy-5-hydroxymethyl-2-oxotetrahydrofuran-3-yl)carbamic acid benzyl ester

benzyl chloroformate

(2S,3S,4R)-3,4,5-trihydroxy-2-amino pentanoic acid

Downstream raw materials:

[(1R,2S,3R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1-hydroxymethyl-butyl]-carbamic acid benzyl ester

2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxycarbonylamino-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl ester

2-(N-benzyloxycarbonyl)amino-2-deoxy-3,4,5-tri(tert-butyldimethylsilyloxy)-1-pivaloyl-D-arabinitol

(S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester