(1R,5R,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-acetoxy-2,7-dioxabicyclo[3.2.1]octane

Base Information

• Chemical Name: (1R,5R,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-acetoxy-2,7-dioxabicyclo[3.2.1]octane
• CAS No.: 1279011-53-8
• Molecular Formula: C₂₃H₂₆O₆
• Molecular Weight: 398.456

Synonyms:(1R,5R,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-acetoxy-2,7-dioxabicyclo[3.2.1]octane

Chemical Property of (1R,5R,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-acetoxy-2,7-dioxabicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

Technology Process of (1R,5R,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-acetoxy-2,7-dioxabicyclo[3.2.1]octane

There total 9 articles about (1R,5R,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-acetoxy-2,7-dioxabicyclo[3.2.1]octane 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: 82.0%

(1R,5S,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-hydroxy-2,7-dioxabicyclo[3.2.1]octane (1279011-52-7) + acetic anhydride (108-24-7) → (1R,5R,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-acetoxy-2,7-dioxabicyclo[3.2.1]octane (1279011-53-8)

Guidance literature:

With pyridine; for 6h; Inert atmosphere;

DOI:10.1021/jo102193q

Reference yield:

C25H32O7 → (1R,5R,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-acetoxy-2,7-dioxabicyclo[3.2.1]octane (1279011-53-8)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium periodate / water; acetone / 2 h / 0 °C / Inert atmosphere

2: sodium tetrahydroborate / tetrahydrofuran; water / 0.5 h / Inert atmosphere; Cooling with ice

3: trifluoroacetic acid / water / 3 h / 0 - 20 °C / Inert atmosphere

4: pyridine / 6 h / Inert atmosphere

With pyridine; sodium tetrahydroborate; sodium periodate; trifluoroacetic acid; In tetrahydrofuran; water; acetone;

DOI:10.1021/jo102193q

Reference yield:

1,2-O-isopropylidene-3-C-(1-acetaldehydo)-3,5-di-O-benzyl-α-D-ribofuranose (1279011-50-5) → (1R,5R,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-acetoxy-2,7-dioxabicyclo[3.2.1]octane (1279011-53-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / tetrahydrofuran; water / 0.5 h / Inert atmosphere; Cooling with ice

2: trifluoroacetic acid / water / 3 h / 0 - 20 °C / Inert atmosphere

3: pyridine / 6 h / Inert atmosphere

With pyridine; sodium tetrahydroborate; trifluoroacetic acid; In tetrahydrofuran; water;

DOI:10.1021/jo102193q

upstream raw materials:

1,2-O-isopropylidene-3-C-(1-acetaldehydo)-3,5-di-O-benzyl-α-D-ribofuranose

1,2-O-isopropylidene-3-C-(2-hydroxyethyl)-3,5-di-O-benzyl-α-D-ribofuranose

(1R,5S,6R,8R)-5-O-benzyl-6-benzyloxymethyl-8-hydroxy-2,7-dioxabicyclo[3.2.1]octane

acetic anhydride

Downstream raw materials:

C₂₆H₂₉N₅O₅

C₃₅H₃₅N₅O₇

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