Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-yl ester

Base Information

• Chemical Name: Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-yl ester
• CAS No.: 628292-86-4
• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.422

Synonyms:Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-yl ester

Chemical Property of Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-yl ester

Chemical Property:

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Technology Process of Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-yl ester

There total 1 articles about Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-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: 89.0%

acetic anhydride (108-24-7) + (1S,3R,4R,5S,8R)-8-benzyloxy-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane (26922-94-1) → Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-yl ester (628292-86-4)

Guidance literature:

With sulfuric acid; acetic acid; at 0 ℃; for 0.833333h;

DOI:10.1081/SCC-120021846

Reference yield: 99.3%

Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-yl ester (628292-86-4) → 3,6-anhydro-5-O-benzyl-1,2-dihydroxy-α,β-D-glucofuranose

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1081/SCC-120021846

Reference yield: 36.0%

2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) + Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-yl ester (628292-86-4) → 1-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-thymine (475558-28-2) + 1-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-α-D-glucofuranosyl)thymine (628292-87-5)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1081/SCC-120021846

upstream raw materials:

acetic anhydride

(1S,3R,4R,5S,8R)-8-benzyloxy-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane

Downstream raw materials:

1-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-thymine

1-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-α-D-glucofuranosyl)thymine

1,2-di-O-acetyl-3,6-anhydro-5-O-benzyl-α,β-D-glucofuranose

1-(3',6'-anhydro-5'-O-benzyl-α-D-glucofuranosyl)thymine

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