1-<(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-11-chloro-6,10,11-trideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil

Base Information

• Chemical Name: 1-<(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-11-chloro-6,10,11-trideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil
• CAS No.: 95069-13-9
• Molecular Formula: C₃₃H₃₈ClN₃O₁₆
• Molecular Weight: 768.128
• Mol file: 95069-13-9.mol

Synonyms:

Chemical Property of 1-<(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-11-chloro-6,10,11-trideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-11-chloro-6,10,11-trideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil

There total 1 articles about 1-<(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-11-chloro-6,10,11-trideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil 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: 74.0%

Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[(R)-1-acetoxy-2-((2R,3S,4R,5R)-3,4,6-triacetoxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-yl)-ethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (95069-12-8,102850-69-1,102850-70-4,104530-19-0) → 1-<(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-11-chloro-6,10,11-trideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil (95069-13-9,102850-71-5)

Guidance literature:

With hydrogenchloride; acetyl chloride; for 14h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90698-0

Reference yield: 18.0%

2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propionyl-α-D-glucopyranose (95069-11-7) + 1-<(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-11-chloro-6,10,11-trideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil (95069-13-9,102850-71-5) → 1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-β-D-glucopyranosyl)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil (95069-14-0,102850-72-6,102850-73-7,117405-60-4,117405-61-5) + 1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-α-D-glucopyranosyl)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil (95069-14-0,102850-72-6,102850-73-7,117405-60-4,117405-61-5)

Guidance literature:

With 4 A molecular sieve; silver perchlorate; silver carbonate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90698-0

Reference yield: 15.0%

1-<(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-11-chloro-6,10,11-trideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil (95069-13-9,102850-71-5) + 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-α-D-galactopyranose (117299-95-3) → 1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-α-D-galactopyranosyl)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)-amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil (95069-14-0,102850-72-6,102850-73-7,117405-60-4,117405-61-5) + 1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-β-D-galactopyranosyl)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)-amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil (95069-14-0,102850-72-6,102850-73-7,117405-60-4,117405-61-5)

Guidance literature:

With molecular sive 4A; In dichloromethane; for 0.666667h; Ambient temperature;

DOI:10.1016/0008-6215(88)85106-1

upstream raw materials:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[(R)-1-acetoxy-2-((2R,3S,4R,5R)-3,4,6-triacetoxy-5-benzyloxycarbonylamino-tetrahydro-pyran-2-yl)-ethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Downstream raw materials:

1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-β-D-glucopyranosyl)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil

1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-α-D-glucopyranosyl)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil

1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-α-D-galactopyranosyl)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)-amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil

1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-β-D-galactopyranosyl)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)-amino-6,10-dideoxy-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil