Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 212266-52-9
• Molecular Formula: C₃₉H₄₄O₁₃
• Molecular Weight: 720.771

Synonyms:Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester

There total 6 articles about Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl 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: 52.2%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester (212266-51-8) → Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester (212266-52-9)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; for 6h; Ambient temperature;

DOI:10.1080/07328309808002338

Reference yield:

2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (212266-42-7) → Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester (212266-52-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / pyridine / 17 h / Ambient temperature

2: 88 percent / H₂ / Pd/C / ethanol; dioxane / 2 h / 825.07 Torr / Ambient temperature

3: 67 percent / H₂ / Pd/C / ethanol; dioxane / 5 h / 825.07 Torr / Ambient temperature

4: 71 percent / ZnCl₂ / 4 h / Ambient temperature

5: 52.2 percent / TfOH / CH₂Cl₂; cyclohexane / 6 h / Ambient temperature

With trifluorormethanesulfonic acid; hydrogen; zinc(II) chloride; palladium on activated charcoal; In 1,4-dioxane; pyridine; ethanol; dichloromethane; cyclohexane;

DOI:10.1080/07328309808002338

Reference yield:

Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (212266-49-4) → Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester (212266-52-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / H₂ / Pd/C / ethanol; dioxane / 5 h / 825.07 Torr / Ambient temperature

2: 71 percent / ZnCl₂ / 4 h / Ambient temperature

3: 52.2 percent / TfOH / CH₂Cl₂; cyclohexane / 6 h / Ambient temperature

With trifluorormethanesulfonic acid; hydrogen; zinc(II) chloride; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; cyclohexane;

DOI:10.1080/07328309808002338

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4R,6R)-4-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside

C₄₅H₆₀O₂₀

Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-acetoxymethyl-6-((2R,3R,4S,5R,6R)-3,4-bis-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

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