(R)-1-((2R,3S,4R,5R)-3-(benzyloxy)-4-hydroxy-5-methoxytetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate

Base Information

• Chemical Name: (R)-1-((2R,3S,4R,5R)-3-(benzyloxy)-4-hydroxy-5-methoxytetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate
• CAS No.: 1610605-76-9
• Molecular Formula: C₂₈H₂₈O₈
• Molecular Weight: 492.526
• Mol file: 1610605-76-9.mol

Synonyms:(R)-1-((2R,3S,4R,5R)-3-(benzyloxy)-4-hydroxy-5-methoxytetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate

Chemical Property of (R)-1-((2R,3S,4R,5R)-3-(benzyloxy)-4-hydroxy-5-methoxytetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((2R,3S,4R,5R)-3-(benzyloxy)-4-hydroxy-5-methoxytetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate

There total 5 articles about (R)-1-((2R,3S,4R,5R)-3-(benzyloxy)-4-hydroxy-5-methoxytetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate 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:

methanol (67-56-1) + (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diyl dibenzoate (801316-36-9) → (R)-1-((2R,3S,4R,5R)-3-(benzyloxy)-4-hydroxy-5-methoxytetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate (1610605-76-9)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 96h;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

Diacetone D-glucose (2595-05-3) → (R)-1-((2R,3S,4R,5R)-3-(benzyloxy)-4-hydroxy-5-methoxytetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate (1610605-76-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere

1.2: 4.5 h / 0 °C

2.1: acetic acid / water / 72 h / 20 °C

3.1: pyridine / acetonitrile / 0 - 60 °C

4.1: hydrogenchloride / 1,4-dioxane / 96 h / 20 °C

With pyridine; hydrogenchloride; sodium hydride; acetic acid; In 1,4-dioxane; water; acetonitrile; mineral oil;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

benzyl bromide (100-39-0) → (R)-1-((2R,3S,4R,5R)-3-(benzyloxy)-4-hydroxy-5-methoxytetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate (1610605-76-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / mineral oil; acetonitrile / 1 h / 0 °C / Inert atmosphere

1.2: 4.5 h / 0 °C

2.1: acetic acid / water / 72 h / 20 °C

3.1: pyridine / acetonitrile / 0 - 60 °C

4.1: hydrogenchloride / 1,4-dioxane / 96 h / 20 °C

With pyridine; hydrogenchloride; sodium hydride; acetic acid; In 1,4-dioxane; water; acetonitrile; mineral oil;

DOI:10.1016/j.bmcl.2014.04.050

upstream raw materials:

Diacetone D-glucose

benzyl bromide

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

methanol

Downstream raw materials:

(R)-1-((2R,3S,4R,5S)-3-(benzyloxy)-4-hydroxy-5-methoxytetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate

(R)-1-((2R,3R,4R,5S)-3-(benzyloxy)-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-yl)ethane-1,2-diyl dibenzoate

(R)-1-((2R,3R,4R,5S)-3-(benzyloxy)-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-yl)ethane-1,2-diol

(2S,3R,4R,5S)-3-(benzyloxy)-4-hydroxy-5-methoxy-4-methyltetrahydrofuran-2-carbaldehyde

Refernces