((2R,3S,4R,5S)-3,4,5-trihydroxy-3-methyltetrahydrofuran-2-yl)methyl benzoate

Base Information

• Chemical Name: ((2R,3S,4R,5S)-3,4,5-trihydroxy-3-methyltetrahydrofuran-2-yl)methyl benzoate
• CAS No.: 89157-83-5
• Molecular Formula: C₁₃H₁₆O₆
• Molecular Weight: 268.266
• Mol file: 89157-83-5.mol

Synonyms:((2R,3S,4R,5S)-3,4,5-trihydroxy-3-methyltetrahydrofuran-2-yl)methyl benzoate

Chemical Property of ((2R,3S,4R,5S)-3,4,5-trihydroxy-3-methyltetrahydrofuran-2-yl)methyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3S,4R,5S)-3,4,5-trihydroxy-3-methyltetrahydrofuran-2-yl)methyl benzoate

There total 14 articles about ((2R,3S,4R,5S)-3,4,5-trihydroxy-3-methyltetrahydrofuran-2-yl)methyl benzoate 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:

((3aR,5R,6R,6aR)-6-hydroxy-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (16831-81-5) → ((2R,3S,4R,5S)-3,4,5-trihydroxy-3-methyltetrahydrofuran-2-yl)methyl benzoate (89157-83-5)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 0.5h;

Reference yield:

((3aR,5R,6R,6aR)-6-hydroxy-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (16831-81-5) → 5-O-benzoyl-3-C-methyl-α,β-D-ribofuranose (89157-83-5,89157-84-6)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 0.333333h;

DOI:10.1016/0008-6215(88)84024-2

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) → 5-O-benzoyl-3-C-methyl-α,β-D-ribofuranose (89157-83-5,89157-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂

2: TFA / H₂O

With trifluoroacetic acid; In dichloromethane; water;

DOI:10.1021/jm048944c

upstream raw materials:

((3aR,5R,6R,6aR)-6-hydroxy-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose

5-O-benzoyl-α-D-xylofuranose

1,2;5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose

Downstream raw materials:

(3R,4R,5R)-5-((benzoyloxy)methyl)-4-methyltetrahydrofuran-2,3,4-triyl triacetate

1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α-D-ribofuranose

1-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil

1-(5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)uracil 2'-(2-cyanoethyl phosphate)