2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: 2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 4-nitro-benzyl ester
• CAS No.: 79416-08-3
• Molecular Formula: C₃₂H₃₄N₂O₁₀
• Molecular Weight: 606.629
• Mol file: 79416-08-3.mol

Synonyms:2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 4-nitro-benzyl ester

Chemical Property of 2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 4-nitro-benzyl ester

There total 1 articles about 2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 4-nitro-benzyl 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: 75.0%

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(D-1-carboxyethyl)-α-D-glucopyranoside (15008-41-0) + 4-nitrobenzyl tosylate (4450-68-4) → 2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 4-nitro-benzyl ester (79416-08-3)

Guidance literature:

In acetone; for 2h; Heating;

DOI:10.1016/S0040-4039(01)92921-1

Reference yield:

2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 4-nitro-benzyl ester (79416-08-3) → 2-[(2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yloxy]-propionic acid 4-nitro-benzyl ester (79427-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 60percent aqueous acetic acid / 1 h / Heating

2: pyridine / 1 h / 0 °C

With acetic acid; In pyridine;

DOI:10.1016/S0040-4039(01)92921-1

Reference yield:

2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid 4-nitro-benzyl ester (79416-08-3) → Hexadecanoic acid (R)-2-{[2-({(2R,3R,4R,5R,6S)-5-acetylamino-6-benzyloxy-3-hydroxy-4-[1-(4-nitro-benzyloxycarbonyl)-ethoxy]-tetrahydro-pyran-2-ylmethyl}-amino)-ethoxy]-hydroxy-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester (79416-10-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 60percent aqueous acetic acid / 1 h / Heating

2: pyridine / 1 h / 0 °C

3: 55 percent / triethylamine / CHCl₃ / 15 h / 80 - 90 °C / sealed tube

With acetic acid; triethylamine; In pyridine; chloroform;

DOI:10.1016/S0040-4039(01)92921-1

upstream raw materials:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(D-1-carboxyethyl)-α-D-glucopyranoside

4-nitrobenzyl tosylate

Downstream raw materials:

2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionic acid 4-nitro-benzyl ester

2-[(2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yloxy]-propionic acid 4-nitro-benzyl ester

Hexadecanoic acid (R)-2-{[2-({(2R,3R,4R,5R,6S)-5-acetylamino-6-benzyloxy-3-hydroxy-4-[1-(4-nitro-benzyloxycarbonyl)-ethoxy]-tetrahydro-pyran-2-ylmethyl}-amino)-ethoxy]-hydroxy-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester