benzyl (2R,3'R)-3-[3-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)propyl-hydroxy-phosphinoyloxy]-2-(3',7'-dimethyloctyloxy)propanoate

Base Information

• Chemical Name: benzyl (2R,3'R)-3-[3-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)propyl-hydroxy-phosphinoyloxy]-2-(3',7'-dimethyloctyloxy)propanoate
• CAS No.: 828930-61-6
• Molecular Formula: C₄₉H₇₅N₂O₂₂P
• Molecular Weight: 1075.11

Synonyms:

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

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Useful:

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

There total 7 articles about benzyl (2R,3'R)-3-[3-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)propyl-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:

(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-[3-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)propyl-hydroxy-phosphinoyloxy]-2-(3',7'-dimethyloctyloxy)propanoate (828930-61-6)

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: 72 percent / trichloroacetonitrile; pyridine / 96 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-[3-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)propyl-hydroxy-phosphinoyloxy]-2-(3',7'-dimethyloctyloxy)propanoate (828930-61-6)

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: 72 percent / trichloroacetonitrile; pyridine / 96 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

Reference yield:

(2R,3'R)-3-hydroxy-2-(3',7'-dimethyloctyloxy)propanoic acid (828930-49-0) → benzyl (2R,3'R)-3-[3-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)propyl-hydroxy-phosphinoyloxy]-2-(3',7'-dimethyloctyloxy)propanoate (828930-61-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / sodium hydrogen carbonate / dimethylformamide / 24 h / 70 °C

2: 72 percent / trichloroacetonitrile; pyridine / 96 h / 70 °C

With pyridine; sodium hydrogencarbonate; trichloroacetonitrile; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.09.019

upstream raw materials:

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

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

(3'R)-1,3:4,6-di-O-benzylidene-2,5-di-O-(3',7'-dimethyl-6'-octenyl)-D-mannitol

3-bromopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside

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