2-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-propenyloxy-tetrahydro-pyran-4-yloxy]-propionic acid

Base Information

• Chemical Name: 2-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-propenyloxy-tetrahydro-pyran-4-yloxy]-propionic acid
• CAS No.: 877462-23-2
• Molecular Formula: C₄₃H₅₂N₂O₁₃
• Molecular Weight: 804.891

Synonyms:2-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-propenyloxy-tetrahydro-pyran-4-yloxy]-propionic acid

Chemical Property of 2-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-propenyloxy-tetrahydro-pyran-4-yloxy]-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 2-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-propenyloxy-tetrahydro-pyran-4-yloxy]-propionic acid

There total 6 articles about 2-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-propenyloxy-tetrahydro-pyran-4-yloxy]-propionic acid 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: 100.0%

1-propenyl 2-acetylamino-6-O-benzyl-4-O-(2-acetylamino)-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-3-O-((R)-1-(ethoxycarbonyl)ethyl)-2-deoxy-α-D-glucopyranoside (877462-10-7) → 2-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-propenyloxy-tetrahydro-pyran-4-yloxy]-propionic acid (877462-23-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; at 20 ℃; for 1h;

DOI:10.1039/b511866b

Reference yield:

allyl 6-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-3-O-((R)-1-(ethoxycarbonyl)ethyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (391860-85-8) → 2-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-propenyloxy-tetrahydro-pyran-4-yloxy]-propionic acid (877462-23-2)

Guidance literature:

Multi-step reaction with 4 steps

1: AcOH; Zn/Cu / 4 h / 20 °C

2: pyridine / 24 h / 20 °C

3: 99 percent / H₂ [Ir(cod)(MePh₂P)2]PF₆ / [Ir(cod)(MePh₂P)2]PF₆ / tetrahydrofuran / 7 h / 20 °C

4: 100 percent / aq. LiOH / dioxane; tetrahydrofuran / 1 h / 20 °C

With pyridine; lithium hydroxide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen; copper; acetic acid; zinc; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1039/b511866b

Reference yield:

2-[2-allyloxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-propionic acid ethyl ester → 2-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-propenyloxy-tetrahydro-pyran-4-yloxy]-propionic acid (877462-23-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.17 h / -15 °C

2: AcOH; Zn/Cu / 4 h / 20 °C

3: pyridine / 24 h / 20 °C

4: 99 percent / H₂ [Ir(cod)(MePh₂P)2]PF₆ / [Ir(cod)(MePh₂P)2]PF₆ / tetrahydrofuran / 7 h / 20 °C

5: 100 percent / aq. LiOH / dioxane; tetrahydrofuran / 1 h / 20 °C

With pyridine; lithium hydroxide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; copper; acetic acid; zinc; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1039/b511866b

upstream raw materials:

1-propenyl 2-acetylamino-6-O-benzyl-4-O-(2-acetylamino)-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-3-O-((R)-1-(ethoxycarbonyl)ethyl)-2-deoxy-α-D-glucopyranoside

1-allyl 2-acetylamino-6-O-benzyl-4-O-(2'-acetylamino-3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-α-D-glucopyranoside

allyl 6-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-3-O-((R)-1-(ethoxycarbonyl)ethyl)-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

2,2,2-Trichloro-acetimidic acid (2R,4aR,7R,8R,8aS)-8-benzyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

Downstream raw materials:

C₇₂H₈₉N₇O₁₉

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