3-aza-3-deoxy-1,2:6,7-di-O-isopropylidene-3-(p-nitrophenylamino)-α-D-ribo-hepto-1,5-pyranos-4-ulose

Base Information

• Chemical Name: 3-aza-3-deoxy-1,2:6,7-di-O-isopropylidene-3-(p-nitrophenylamino)-α-D-ribo-hepto-1,5-pyranos-4-ulose
• CAS No.: 52366-47-9
• Molecular Formula: C₁₈H₂₃N₃O₈
• Molecular Weight: 409.396
• Mol file: 52366-47-9.mol

Synonyms:3-aza-3-deoxy-1,2:6,7-di-O-isopropylidene-3-(p-nitrophenylamino)-α-D-ribo-hepto-1,5-pyranos-4-ulose

Chemical Property of 3-aza-3-deoxy-1,2:6,7-di-O-isopropylidene-3-(p-nitrophenylamino)-α-D-ribo-hepto-1,5-pyranos-4-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-aza-3-deoxy-1,2:6,7-di-O-isopropylidene-3-(p-nitrophenylamino)-α-D-ribo-hepto-1,5-pyranos-4-ulose

There total 5 articles about 3-aza-3-deoxy-1,2:6,7-di-O-isopropylidene-3-(p-nitrophenylamino)-α-D-ribo-hepto-1,5-pyranos-4-ulose 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: 57.0%

3-aza-3-deoxy-1,2-O-isopropylidene-3-(p-nitrophenylamino)-α-L-glyceropentopyranos-4-ulose (119720-36-4) → 3-aza-3-deoxy-1,2:6,7-di-O-isopropylidene-3-(p-nitrophenylamino)-α-D-ribo-hepto-1,5-pyranos-4-ulose (52366-47-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1016/0008-6215(88)84026-6

Reference yield:

4-Nitro-phenylhydrazon der O1,O2-Isopropyliden-α-L-glycero-3-tetrosulo-furanose (29360-16-5,52340-58-6) → 3-aza-3-deoxy-1,2:6,7-di-O-isopropylidene-3-(p-nitrophenylamino)-α-D-ribo-hepto-1,5-pyranos-4-ulose (52366-47-9)

Guidance literature:

Multi-step reaction with 4 steps

2: NaOMe / methanol

3: 32 percent / tert-BuOK / tetrahydrofuran / 20 h / 20 °C

4: 57 percent / tert-BuOK / tetrahydrofuran / 20 h / 20 °C

With potassium tert-butylate; sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1016/0008-6215(88)84026-6

Reference yield:

C15H17N3O7 (29360-17-6,29360-22-3,52340-57-5) → 3-aza-3-deoxy-1,2:6,7-di-O-isopropylidene-3-(p-nitrophenylamino)-α-D-ribo-hepto-1,5-pyranos-4-ulose (52366-47-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / methanol

2: 32 percent / tert-BuOK / tetrahydrofuran / 20 h / 20 °C

3: 57 percent / tert-BuOK / tetrahydrofuran / 20 h / 20 °C

With potassium tert-butylate; sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1016/0008-6215(88)84026-6

upstream raw materials:

3-aza-3-deoxy-1,2-O-isopropylidene-3-(p-nitrophenylamino)-α-L-glyceropentopyranos-4-ulose

4-Nitro-phenylhydrazon der O¹,O²-Isopropyliden-α-L-glycero-3-tetrosulo-furanose

C₁₅H₁₇N₃O₇

(3aS,6R,6aS)-2,2-Dimethyl-6-(4-nitro-phenylazo)-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

Downstream raw materials:

N-[(3aR)-5c-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-oxo-(3ar,7ac)-tetrahydro-[1,3]dioxolo[4,5-b][1,4]oxazin-7-yl]-N-(4-nitro-phenyl)-acetamide

3-aza-3-deoxy-1,2:6,7-di-O-isopropylidene-3-(p-nitrophenylacetamido)-α-D-ribo-hepto-1,5-pyranos-4-ulose