benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate

Base Information

• Chemical Name: benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate
• CAS No.: 828930-51-4
• Molecular Formula: C₆₂H₈₂NO₁₉P
• Molecular Weight: 1176.3
• Mol file: 828930-51-4.mol

Synonyms:benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate

Chemical Property of benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate

There total 12 articles about benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate 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: 98.0%

benzyl (2R,3'R)-3-hydroxy-2-(3',7'-dimethyloctyloxy)propanoate (828930-50-3) + (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonic acid (149359-32-0) → benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate (828930-51-4)

Guidance literature:

With pyridine; trichloroacetonitrile; at 70 ℃; for 42h;

DOI:10.1016/j.bmc.2004.09.019

Reference yield:

(3'R)-1,3:4,6-di-O-benzylidene-2,5-di-O-(3',7'-dimethyl-6'-octenyl)-D-mannitol (828930-47-8) → benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate (828930-51-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 40 percent / hydrogen; acetic acid / palladium on carbon / 36 h

2: sodium periodate / tetrahydrofuran; H₂O / 1 h / 50 °C

3: 215 mg / silver(I) oxide; sodium hydroxide / tetrahydrofuran; H₂O / 18 h

4: 77 percent / sodium hydrogen carbonate / dimethylformamide / 24 h / 70 °C

5: 98 percent / trichloroacetonitrile; pyridine / 42 h / 70 °C

With pyridine; sodium hydroxide; sodium periodate; hydrogen; sodium hydrogencarbonate; acetic acid; trichloroacetonitrile; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.09.019

Reference yield:

(R)-2-((R)-3,7-Dimethyl-octyloxy)-3-hydroxy-propionaldehyde → benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate (828930-51-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 215 mg / silver(I) oxide; sodium hydroxide / tetrahydrofuran; H₂O / 18 h

2: 77 percent / sodium hydrogen carbonate / dimethylformamide / 24 h / 70 °C

3: 98 percent / trichloroacetonitrile; pyridine / 42 h / 70 °C

With pyridine; sodium hydroxide; sodium hydrogencarbonate; trichloroacetonitrile; silver(l) oxide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.09.019

upstream raw materials:

benzyl (2R,3'R)-3-hydroxy-2-(3',7'-dimethyloctyloxy)propanoate

(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonic acid

(2R,3'R)-3-hydroxy-2-(3',7'-dimethyloctyloxy)propanoic acid

(3'R)-2,5-di-O-(3',7'-dimethyloctyl)-D-mannitol