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

Base Information

• Chemical Name: 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
• CAS No.: 87256-63-1
• Molecular Formula: C₂₈H₃₈N₂O₁₃
• Molecular Weight: 610.615

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose (26775-14-4) → 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)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / aq. acetic acid

3: 98 percent / NaI

4: 43 percent / sodium nitrile

5: 2.) KF / 2.) acetonitrile

6: acetic anhydride, pyridene / CHCl₃

7: NaBH₄

With potassium fluoride; sodium tetrahydroborate; sodium nitrile; acetic anhydride; acetic acid; sodium iodide; phenazopyridine hydrochloride; In chloroform;

DOI:10.1246/cl.1983.819

Reference yield:

3'-O-acetyl-1',2'-O-isopropylidene-5',6'-diol-α-D-allofuranose (51433-05-7) → 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)

Guidance literature:

Multi-step reaction with 6 steps

2: 98 percent / NaI

3: 43 percent / sodium nitrile

4: 2.) KF / 2.) acetonitrile

5: acetic anhydride, pyridene / CHCl₃

6: NaBH₄

With potassium fluoride; sodium tetrahydroborate; sodium nitrile; acetic anhydride; sodium iodide; phenazopyridine hydrochloride; In chloroform;

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 (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)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) KF / 2.) acetonitrile

2: acetic anhydride, pyridene / CHCl₃

3: NaBH₄

With potassium fluoride; sodium tetrahydroborate; acetic anhydride; phenazopyridine hydrochloride; In chloroform;

DOI:10.1246/cl.1983.819

upstream raw materials:

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose

3'-O-acetyl-1',2'-O-isopropylidene-5',6'-diol-α-D-allofuranose

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

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)

Downstream raw materials:

{(3aS,4R,6S,7R,7aR)-4-[(S)-2-Hydroxy-2-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-carbamic acid benzyl ester

{(3aS,4R,6S,7R,7aR)-4-[(R)-2-Hydroxy-2-((3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-carbamic acid benzyl ester

Acetic acid (S)-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

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

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