benzyl (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-octyloxypropanoate

Base Information

• Chemical Name: benzyl (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-octyloxypropanoate
• CAS No.: 149359-37-5
• Molecular Formula: C₆₀H₇₈NO₁₉P
• Molecular Weight: 1148.25

Synonyms:benzyl (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-octyloxypropanoate

Chemical Property of benzyl (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-octyloxypropanoate

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Technology Process of benzyl (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-octyloxypropanoate

There total 14 articles about benzyl (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-octyloxypropanoate 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: 78.0%

benzyl (R)-3-hydroxy-2-octyloxypropanoate (149359-36-4) + (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 (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-octyloxypropanoate (149359-37-5)

Guidance literature:

With pyridine; trichloroacetonitrile;

DOI:10.1021/jo00065a004

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride (7772-87-4) → benzyl (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-octyloxypropanoate (149359-37-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 83 percent / silver(I) trifluoromethanesulfonate; collidine; molecular sieves 4 Angstroem / CH₂Cl₂ / -30 - 20 °C

2.1: hydrazine hydrate / ethanol; H₂O / 1.5 h / 80 °C

2.2: 88 percent / pyridine / 12 h

3.1: bromotrimethylsilane / CH₂Cl₂ / 2 h

3.2: 91 percent / water / acetone / 0.33 h

4.1: 78 percent / trichloroacetonitrile; pyridine / 42 h / 70 °C

With pyridine; 2,3,5-trimethyl-pyridine; trimethylsilyl bromide; 4 A molecular sieve; silver trifluoromethanesulfonate; hydrazine hydrate; trichloroacetonitrile; In ethanol; dichloromethane; water;

DOI:10.1016/j.bmc.2004.09.019

Reference yield:

(R)-3-hydroxy-2-octyloxypropanoic acid (149359-35-3) → benzyl (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-octyloxypropanoate (149359-37-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / sodium hydrogen carbonate / dimethylformamide / 24 h / 70 °C

2: 78 percent / trichloroacetonitrile; pyridine / 42 h / 70 °C

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

DOI:10.1016/j.bmc.2004.09.019

upstream raw materials:

benzyl (R)-3-hydroxy-2-octyloxypropanoate

(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

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride

1-bromo-octane

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