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

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[(S)-1-acetoxy-2-((2R,3S,4R,5R,6S)-3,4-diacetoxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 87256-68-6
• Molecular Formula: C₃₄H₄₁N₃O₁₇
• Molecular Weight: 763.709
• Mol file: 87256-68-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[(S)-1-acetoxy-2-((2R,3S,4R,5R,6S)-3,4-diacetoxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl 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:

3-O-acetyl-5-deoxy-1,2-O-isopropylidene-5-nitro-α-D-ribofuranose (87256-61-9) → 1-<(11S)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-6,10-dideoxy-11-O-methyl-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil (87256-68-6,99881-65-9,102850-68-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 2.) KF / 2.) acetonitrile

2: acetic anhydride, pyridene / CHCl₃

3: NaBH₄

5: 87 percent / pyridine

6: 60 percent aq. acetic acid / Heating

7: pyridine

8: 74.5 percent / SnCl₄ / 1,2-dichloro-ethane

With pyridine; potassium fluoride; sodium tetrahydroborate; acetic anhydride; tin(IV) chloride; acetic acid; phenazopyridine hydrochloride; In chloroform; 1,2-dichloro-ethane;

DOI:10.1246/cl.1983.819

Reference yield:

3-O-acetyl-5-deoxy-1,2-O-isopropylidene-5-nitro-α-D-ribofuranose (87256-61-9) → Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[(S)-1-acetoxy-2-((2R,3S,4R,5R,6S)-3,4-diacetoxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (87256-68-6,99881-65-9,102850-68-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 2.) KF / 2.) acetonitrile

2: acetic anhydride, pyridene / CHCl₃

3: NaBH₄

5: pyridine

6: 60 percent aq. acetic acid / Heating

7: pyridine

8: SnCl₄ / 1,2-dichloro-ethane

With pyridine; potassium fluoride; sodium tetrahydroborate; acetic anhydride; tin(IV) chloride; acetic acid; phenazopyridine hydrochloride; In chloroform; 1,2-dichloro-ethane;

DOI:10.1246/cl.1983.819

Reference yield:

Acetic acid (3aR,5R,6R,6aR)-5-[2-((3aS,4R,6S,7R,7aR)-7-benzyloxycarbonylamino-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-nitro-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (87256-63-1) → 1-<(11S)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)amino-6,10-dideoxy-11-O-methyl-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil (87256-68-6,99881-65-9,102850-68-0)

Guidance literature:

Multi-step reaction with 5 steps

2: 87 percent / pyridine

3: 60 percent aq. acetic acid / Heating

4: pyridine

5: 74.5 percent / SnCl₄ / 1,2-dichloro-ethane

With pyridine; tin(IV) chloride; acetic acid; In 1,2-dichloro-ethane;

DOI:10.1246/cl.1983.819

upstream raw materials:

3-O-acetyl-5-deoxy-1,2-O-isopropylidene-5-nitro-α-D-ribofuranose

Acetic acid (3aR,5R,6R,6aR)-5-[2-((3aS,4R,6S,7R,7aR)-7-benzyloxycarbonylamino-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-nitro-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

methyl-9-O-acetyl-2-(benzyloxycarbonyl)amino-2,7-dideoxy-3,4:10,11-di-O-isopropylidene-7-nitro-β-L-undecodialdo-(11R)-furanose-(11,8)-pyranoside-(1,5)

Acetic acid (R)-1-((3aR,5R,6R,6aR)-6-acetoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-((3aS,4R,6S,7R,7aR)-7-benzyloxycarbonylamino-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-ethyl ester

Downstream raw materials:

1-<(11R)-1,3,4,7,9,10-Hexa-O-acetyl-2-<(benzyloxycarbonyl)amino>-2,6-dideoxy-L-allo-α-D-galacto-undecodialdo-1,5-pyranose-11,8-furanosyl>uracil

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