Benzoic acid (2S,3R,4S,5S)-3-benzyloxy-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4S,5S)-3-benzyloxy-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 395075-12-4
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.391

Synonyms:Benzoic acid (2S,3R,4S,5S)-3-benzyloxy-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Benzoic acid (2S,3R,4S,5S)-3-benzyloxy-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (2S,3R,4S,5S)-3-benzyloxy-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

There total 3 articles about Benzoic acid (2S,3R,4S,5S)-3-benzyloxy-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl 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:

methanol (67-56-1) + Benzoic acid (3aS,5S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (479035-83-1) → Benzoic acid (2S,3R,4S,5S)-3-benzyloxy-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester (395075-12-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; at 20 ℃; for 1.5h;

DOI:10.1021/ol0168059

Reference yield:

benzyl bromide (100-39-0) → Benzoic acid (2S,3R,4S,5S)-3-benzyloxy-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester (395075-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: TBAI / tetrahydrofuran / 0 - 20 °C

2.1: aq. HCl / dioxane; methanol / 1.5 h / 20 °C

With hydrogenchloride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1021/ol0168059

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-L-ribofuranose (171721-11-2) → Benzoic acid (2S,3R,4S,5S)-3-benzyloxy-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester (395075-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: TBAI / tetrahydrofuran / 0 - 20 °C

2.1: aq. HCl / dioxane; methanol / 1.5 h / 20 °C

With hydrogenchloride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1021/ol0168059

upstream raw materials:

methanol

Benzoic acid (3aS,5S,6S,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

benzyl bromide

5-O-benzoyl-1,2-O-isopropylidene-α-L-ribofuranose

Downstream raw materials:

(-)-N₄-benzoyl-1-[(1S,4S)-5-O-benzoyl-2,3-dideoxy-3,3-difluoro-β-L-ribofuranosyl]cytosine

(+)-N₄-benzoyl-1-[(1R,4S)-5-O-benzoyl-2,3-dideoxy-3,3-difluoro-α-L-ribofuranosyl]cytosine

Benzoic acid (2S,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

1-O-acetyl-5-O-benzoyl-3,3-difluoro-3-deoxo-L-glyceropentofuranosid-3-ulose

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