5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-4-O-phenoxycarbonyl-L-galacto-hept-6-enonamide

Base Information

• Chemical Name: 5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-4-O-phenoxycarbonyl-L-galacto-hept-6-enonamide
• CAS No.: 403709-24-0
• Molecular Formula: C₂₃H₃₅NO₇Si
• Molecular Weight: 465.619
• Mol file: 403709-24-0.mol

Synonyms:5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-4-O-phenoxycarbonyl-L-galacto-hept-6-enonamide

Chemical Property of 5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-4-O-phenoxycarbonyl-L-galacto-hept-6-enonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-4-O-phenoxycarbonyl-L-galacto-hept-6-enonamide

There total 5 articles about 5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-4-O-phenoxycarbonyl-L-galacto-hept-6-enonamide 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: 60.0%

phenyl chloroformate (1885-14-9) + 5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-L-galacto-hept-6-enonamide (342896-28-0) → 5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-4-O-phenoxycarbonyl-L-galacto-hept-6-enonamide (403709-24-0)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(01)00951-6

Reference yield:

methyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid-5-carboxylate (67844-12-6) → 5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-4-O-phenoxycarbonyl-L-galacto-hept-6-enonamide (403709-24-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,N-carbonyldiimidazole / tetrahydrofuran / 0.5 h

1.2: 91 percent / ammonia / tetrahydrofuran / 2 h

2.1: 94 percent / diisobutylaluminium hydride / CH₂Cl₂ / 9 h / -78 °C

3.1: 50 percent / magnesium bromide etherate / CH₂Cl₂ / 49 h / 0 - 20 °C

4.1: 60 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; diisobutylaluminium hydride; magnesium bromide ethyl etherate; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)00951-6

Reference yield:

(+)-dimethyl-2,3-O-isopropylidene-D-tartrate (37031-29-1,6134-82-3,6135-80-4,90613-41-5,116499-08-2,37031-30-4) → 5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-4-O-phenoxycarbonyl-L-galacto-hept-6-enonamide (403709-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 73 percent / KOH / methanol

2.1: N,N-carbonyldiimidazole / tetrahydrofuran / 0.5 h

2.2: 91 percent / ammonia / tetrahydrofuran / 2 h

3.1: 94 percent / diisobutylaluminium hydride / CH₂Cl₂ / 9 h / -78 °C

4.1: 50 percent / magnesium bromide etherate / CH₂Cl₂ / 49 h / 0 - 20 °C

5.1: 60 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; potassium hydroxide; diisobutylaluminium hydride; magnesium bromide ethyl etherate; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)00951-6

upstream raw materials:

phenyl chloroformate

5-O-(tert-butyldimethylsilyl)-6,7-dideoxy-2,3-O-isopropylidene-L-galacto-hept-6-enonamide

(+)-dimethyl-2,3-O-isopropylidene-D-tartrate

methyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid-5-carboxylate